[ CAS No. 647-42-7 ] {[proInfo.proName]}

Name: 647-42-7|3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol|98%
Brand: Ambeed
SKU: A310731
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Quality Control of [ 647-42-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 647-42-7 ]

SDS Specification

Alternatived Products of [ 647-42-7 ]

Product Details of [ 647-42-7 ]

CAS No. :	647-42-7	MDL No. :	MFCD00042143
Formula :	C₈H₅F₁₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GRJRKPMIRMSBNK-UHFFFAOYSA-N
M.W :	364.10	Pubchem ID :	69537
Synonyms :

Calculated chemistry of [ 647-42-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	7
Num. H-bond acceptors :	14.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.62
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.36
Log Po/w (XLOGP3) :	4.37
Log Po/w (WLOGP) :	9.57
Log Po/w (MLOGP) :	4.08
Log Po/w (SILICOS-IT) :	5.08
Consensus Log Po/w :	5.09

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.39
Solubility :	0.0149 mg/ml ; 0.0000409 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.51
Solubility :	0.0112 mg/ml ; 0.0000308 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.99
Solubility :	0.0374 mg/ml ; 0.000103 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.68

Safety of [ 647-42-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P210-P271-P261-P264-P280-P304+P340-P302+P352-P305+P351+P338-P312-P370+P378-P362+P364-P403+P233-P501	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 647-42-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 647-42-7 ]
Downstream synthetic route of [ 647-42-7 ]

[ 647-42-7 ] Synthesis Path-Upstream 1~5

1
[ 647-42-7 ]
[ 79-10-7 ]
[ 17527-29-6 ]

Reference： [1] Journal of Fluorine Chemistry, 1988, vol. 38, # 1, p. 47 - 73
[2] Patent: US2009/23948, 2009, A1, . Location in patent: Page/Page column 5

2
[ 647-42-7 ]
[ 814-68-6 ]
[ 17527-29-6 ]

Reference： [1] Physical Chemistry Chemical Physics, 2002, vol. 4, # 3, p. 507 - 513
[2] Journal of Fluorine Chemistry, 1997, vol. 82, # 2, p. 119 - 124

3
[ 647-42-7 ]
[ 292638-85-8 ]
[ 17527-29-6 ]

Reference： [1] Patent: JP2016/34932, 2016, A, . Location in patent: Paragraph 0039

4
[ 116-14-3 ]
[ 74-85-1 ]
[ 354-64-3 ]
[ 10192-85-5 ]
[ 34395-24-9 ]
[ 647-42-7 ]
[ 865-86-1 ]
[ 25291-17-2 ]
[ 21652-58-4 ]
[ 39239-77-5 ]
[ 678-39-7 ]
[ 30389-25-4 ]
[ 27905-45-9 ]
[ 17527-29-6 ]
[ 17741-60-5 ]

Reference： [1] Patent: EP1757574, 2007, A1, . Location in patent: Page/Page column 8-9

5
[ 2043-57-4 ]
[ 2043-53-0 ]
[ 2043-54-1 ]
[ 30046-31-2 ]
[ 10192-85-5 ]
[ 34395-24-9 ]
[ 647-42-7 ]
[ 865-86-1 ]
[ 25291-17-2 ]
[ 21652-58-4 ]
[ 39239-77-5 ]
[ 678-39-7 ]
[ 30389-25-4 ]
[ 27905-45-9 ]
[ 17527-29-6 ]
[ 17741-60-5 ]

Reference： [1] Patent: EP1757578, 2007, A1, . Location in patent: Page/Page column 6-7; 8-9

[ 647-42-7 ] Synthesis Path-Downstream 1~73

1
[ 78-71-7 ]
[ 647-42-7 ]
3-chloromethyl-3-(1,1,2,2-tetrahydro-perfluoro-octyloxy)methyl oxetane [ No CAS ]
3,3-Bis-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyloxymethyl)-oxetane [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,1993,vol. 65,p. 43 - 48

2
[ 79-41-4 ]
[ 647-42-7 ]
[ 2144-53-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydroquinone;toluene-4-sulfonic acid; In toluene; at 115℃; for 5h;	Toluene (2 L), 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-ol (2.18 kg, 6.0 mol), 2-methyl-2-propenic acid (methacrylic acid) (567 g, 6.6 mol) and 1,4-dihydroxybenzene (hydroquinone) (6.59 g, 60 mmol) were added and then p-toluenesulfonic acid monohydrate (148.06 g, 0.78 mol) was added thereto. The obtained solution was heated and subjected to reflux dehydration at 115 C. for 5 hours. After reflux dehydration, the obtained reaction solution was cooled to around room temperature and added with triethylamine (151.5 g, 1.50 mol) was added thereto, stirred for 0.5 hours and then added with 150 g of silica gel. After stirring for 0.5 hours, the silica gel was filtered off and the obtained filtrate was added with 1,4-dihydroxybenzene (hydroquinone) (1.32 g, 12.0 mmol), and the solvent was removed in vacuum distillation and then was purified in distillation to obtain 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane 2-methyl-2-propenic acid ester (2.44 kg, 94%).

Reference： [1]Patent: US2010/324314,2010,A1 .Location in patent: Page/Page column 15
[2]Journal of Fluorine Chemistry,1988,vol. 38,p. 47 - 73
[3]Angewandte Chemie - International Edition,2019,vol. 58,p. 10941 - 10945
Angew. Chem.,2019,vol. 131,p. 11057 - 11061,5

3
[ 2043-57-4 ]
[ 647-42-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With water; In N,N-dimethyl-formamide; at 125 - 130℃; under 2625.26 Torr; for 32h;Large scale; Green chemistry;	(2) In another 20 liters of pressure-resistant reactor, 2000 g of perfluorohexylethyl iodide obtained in (1) was added, and the mixture was heated to 125 C with stirring. 6000 g of 4% aqueous dimethylformamide was added to the reactor at a rate of 80 g/min by a metering pump, and the temperature was controlled at 125 to 130 C, the pressure was not higher than 0.35 MPa, and the reaction was continued for 32 hours, and the heating was removed. Neutralize with 2222 g of 11.3% potassium hydroxide aqueous solution, separate the organic phase, and then wash once with 2222 g of deionized water, separate the organic phase, and remove the light component to obtain 1420 g of fluoroalcohol 88% and fluorinated olefin 5.5%. Intermediate product.
	With water;copper(II) sulfate; at 275℃; for 300h;Gas phase;Conversion of starting material;	The catalyst of Preparation Example 1 (10 g) was placed in a stainless-steel reaction tube having an inside diameter of 10 mm and length of 250 mm, and was heated to 275 C. with a heater. CF3CF2 (CF2CF2)2CH2CH2I and water were introduced into a vaporizer (preheat phase) at a rate of 2.5 g/hr and 12 g/hr, respectively, with a plunger pump and were vaporized. Air was introduced into the reaction tube as a carrier gas at a rate of 35 cc/min. The vaporized gases were carried to the catalyst by the air to cause a catalytic reaction on the catalyst. Reaction products were recovered with an ice trap and a dry ice/methanol trap provided at the outlet of the reaction tube. The analysis of the products by gas chromatography revealed that an alcohol (CF3CF2 (CF2CF2)2CH2CH2OH) was formed at the degree of conversion of 98% and selectivity of 95%.
	With water;silver nitrate; at 165℃;Gas phase;Conversion of starting material;	The catalyst of Preparation Example 5 (10 g) was placed in a stainless-steel reaction tube having an inside diameter of 10 mm and length of 250 mm, and was heated to 165 C. with a heater. In a manner similar to Example 1, CF3CF2 (CF2CF2) 2CH2CH2I and water were supplied to the catalyst at a rate of 2.5 g/hr and 12 g/hr, respectively, to cause a catalytic reaction on the catalyst. Reaction products were recovered with an ice trap and dry ice/methanol trap provided at the outlet of the reaction tube. The GC analysis of the products revealed that an alcohol (CF3CF2 (CF2CF2)2CH2 CH2OH) was formed at the degree of conversion of 100% and selectivity of 81%.

	With water;silver nitrate; copper(II) sulfate; at 210℃;Conversion of starting material;	Reactions were conducted using the catalysts of the above Preparation Examples 7 to 11 in a manner similar to Example 6 except with a different reaction temperature. The analysis results of the reaction products are shown in the table below.
	With water;mercury(II) sulfate; at 180℃; under 760.051 - 2940.29 Torr;Gas phase;Conversion of starting material;	The catalyst of Preparation Example 6 (15 g) was placed in a stainless-steel reaction tube having an inside diameter of 10 mm and length of 250 mm, and was heated to 180 C. with a heater. CF3CF2 (CF2CF2)2CH2CH2I and water were introduced into a vaporizer at a rate of 2.5 g/hr and 12 g/hr, respectively, and were vaporized. Air was introduced into the reaction tube as a carrier gas at a rate of 35 cc/min. The vaporized gases were carried to the catalyst in the above reaction tube by the air to cause a catalytic reaction on the catalyst. Reaction products were recovered with an ice trap and a dry ice/methanol trap provided at the outlet of the reaction tube. The GC analysis of the products revealed that an alcohol was formed at the degree of conversion of 93% and selectivity of 95%.
	With water;copper(II) sulfate; at 275℃;Conversion of starting material;	Reactions were conducted in a manner similar to Example 1 using the catalysts of the above Preparation Examples 2 to 4. The results of analysis are shown in the table below.
	With potassium hydroxide; In water; dimethyl sulfoxide; N,N-dimethyl-formamide; at 140℃; under 6975.7 Torr; for 11h;	The perfluoroalkyl ethyl iodide, a mixed solvent and water were added to the reaction kettle, the reaction containing perfluoroalkylethanol, by-product olefin, solvent salt and water mixture was added to the rectification column minus Pressure distillation to obtain a distillate and a bottoms liquid, the distillate is a perfluoroalkylethanol, a byproduct mixture of the alkene and water, and the bottom liquid is a solvent salt; and subjecting the obtained distillate to azeotropic distillation to obtain a by-produced olefin And water mixture,And a perfluoroalkylethanol product; subjecting a mixture of by-product olefins and water obtained by azeotropic distillation to standstill liquid separation to obtain a crude by-product olefin and water, and subjecting the crude by-product olefin to a drying treatment to obtain a byproduct olefin product , The water obtained by the separation can be recycled for the hydrolysis of perfluoroalkylethyl iodide;The solvent of the bottom liquid solvent obtained by the vacuum distillation is treated with a strong alkali and then filtered to obtain a mixed solvent and metal iodide. The mixed solvent can be recovered for hydrolysis of perfluoroalkylethyl iodide. Reaction feeding formula shown in Table 1, the reaction parameters and the implementation of control results shown in Table 2.

Reference： [1]Journal of Fluorine Chemistry,1983,vol. 23,p. 57
[2]Patent: CN108911983,2018,A .Location in patent: Paragraph 0024; 0027
[3]Journal of Fluorine Chemistry,1983,vol. 23,p. 57
[4]Tetrahedron,1981,vol. 37,p. 487 - 492
[5]Patent: US6664430,2003,B1 .Location in patent: Page column 7; 9
[6]Patent: US6664430,2003,B1 .Location in patent: Page column 8
[7]Patent: US6664430,2003,B1 .Location in patent: Page column 7-8
[8]Patent: US6664430,2003,B1 .Location in patent: Page column 8
[9]Patent: US6664430,2003,B1 .Location in patent: Page column 8
[10]Patent: US6664430,2003,B1 .Location in patent: Page column 8
[11]Patent: US6664430,2003,B1 .Location in patent: Page column 7-8
[12]Patent: US6664430,2003,B1 .Location in patent: Page column 8; 9
[13]Patent: US6664430,2003,B1 .Location in patent: Page column 7-8
[14]Patent: US6664430,2003,B1 .Location in patent: Page column 8
[15]Patent: US6664430,2003,B1 .Location in patent: Page column 8
[16]Patent: CN107324973,2017,A .Location in patent: Paragraph 0026-0032

4
[ 2043-57-4 ]
[ 647-42-7 ]
[ 25291-17-2 ]
[ 80793-17-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 80 % Spectr. 2: 5 % Spectr. 3: 15 % Spectr.	With water; lithium chloride In N,N-dimethyl-formamide effect of quantity of water and current on electroreduction;

Reference： [1]Benefice-Malouet, S.; Blancou, H.; Calas, P.; Commeyras, A. [Journal of Fluorine Chemistry, 1988, vol. 39, p. 245 - 260]

5
[ 647-42-7 ]
[ 106-95-6 ]
[ 103628-86-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydroxide; at 60℃; under 75.0075 Torr; for 1h;Inert atmosphere; Large scale;	1501.5 g (4.12 mol) of 2- (perfluorohexyl) ethanol (manufactured by NOK Co.: FA-6) and 336.31 g (8.24 mol) of granular NaOH having a weight average particle diameter of 0.7 mm (manufactured by Tosoh Corporation: Toso Pearl) were trained into a 5 L SUS 316 L reaction vessel equipped with a thermometer and a cooling tube. While stirring at 150 rpm using a stirring blade, decompressed to 10 kPa, operation of returning to normal pressure with nitrogen was performed three times, the inside of the tank was replaced with nitrogen. The stirring blade is made of SUS 316L; pitched paddle with a diameter of 75 mm was attached to the upper part of a 75 mm diameter pitched turbine blade with a distance of 35 mm used. Thereafter, it was heated and the temperature was brought to 60 C. Thereto, 755.16 g (6.18 mol) of allyl bromide (manufactured by Wako Pure Chemical Industries, Ltd.) was added drop wise over 180 minutes. Stirring was continued at 60C for 1 hour. The reaction conversion rate after the completion of the reaction was 99.7%. After completion of the reaction, purification was carried out as follows. After cooling the reaction solution to 40C, 1501.5 g of ion exchanged water was added to the reaction tank, after stirring at 150 rpm for 30 minutes, it was left standing and layered. The time from stopping the stirring to separating the layers was within 5 minutes. After checking the layer separation, the upper layer (aqueous layer) was removed, further, 1006.00 g of ion exchanged water was added, after stirring at 150 rpm for 30 minutes, it was left standing and layered. The time from stopping the stirring to separating the layers was within 5 minutes. After checking the layer separation, the upper layer (aqueous layer) was removed. The amount of nonvolatile component after completion of water washing was 0.1%. After completion of water washing, the temperature was raised to 130C. Excess allyl bromide was removed. After removal of allyl bromide, the pressure was reduced to 5 kPa and dehydrated at 60C. After dehydration, decompressed to 2 KPa, distilled at 100C, 1543.00 g of allyl ((perfluorohexyl) ethyl) ether was obtained. The yield was 93% yield. Corrosion was not confirmed in the reaction tank after refining.
88%	With sodium hydroxide; at 60 - 80℃; for 4h;Inert atmosphere;	thermometer,In a 2 L four-necked flask equipped with a condenser tube,800 g (2.2 mol) of FA-6 (manufactured by Unimartech Co., Ltd.) and 175.78 g (4.4 mol) of granular NaOH (manufactured by Wako Pure Chemical Industries, Ltd.) were added. In a nitrogen atmosphere, while stirring at 200 rpm with a Teflon (registered trademark) 12 cm crescent stirring blade, the temperature was heated to 60 C. in the flask. 398.73 g (3.3 mol) of allyl bromide (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise thereto over 2 hours. After completion of the dropwise addition, the mixture was stirred at 70 C. for 1 hour and at 80 C. for 1 hour. Thereafter, the temperature was raised to 130 C. to remove excessive allyl bromide.After cooling to 60 C., 800 g of ion-exchanged water was added, stirred for 30 minutes, then allowed to stand to separate the layers. The upper aqueous layer was withdrawn, 800 g of ion-exchanged water was added, stirred again, allowed to stand still and the aqueous layer was removed. Dehydrated at 60 C./5 kPa and distilled at 100 C./2 kPa to obtain 774.9 g of C 6 F 13 --CH 2 CH 2 --O - CH 2 CHCH 2 (yield 88%) as a fraction.
88%	With sodium hydroxide; at 60 - 80℃; for 4h;Inert atmosphere;	Into a 2 L four-necked flask equipped with a stirrer, a thermometer and a cooling tube,800 g (2.2 mol) of FA-6 (manufactured by Unimartec Co., Ltd.)And 175.78 g (4.4 mol) of granular NaOH (manufactured by Wako Pure Chemical Industries, Ltd.) were added.Under a nitrogen atmosphere,While stirring at 200 rpm with a Teflon (registered trademark) 12 cm crescent stirring blade,The temperature in the flask was brought to 60 C. with heating.398.73 g (3.3 mol) of allyl bromide (manufactured by Wako Pure Chemical Industries, Ltd.)Was added dropwise over 2 hours. After completion of dropping, 1 hour at 70 C.,Followed by stirring at 80 C. for 1 hour. Thereafter, the temperature was raised to 130 C.,Excess allyl bromide was removed.After cooling to 60 C., 800 g of ion-exchanged water was added, stirred for 30 minutes,Thereafter, it was allowed to stand to separate the layers. The upper aqueous layer was extracted,Further, 800 g of ion-exchanged water was added thereto, and the mixture was again stirred, allowed to stand, and the aqueous layer was removed.Dehydrated at 60 C./5 KPa and distilled at 100 C./2 KPa to obtain 774.9 g of C6F13-CH2CH 2-O-CH2CH=CH2(Yield: 88%)

88%	With sodium hydroxide; at 60 - 80℃; for 4h;Inert atmosphere;	C6F13-CH2CH2-O-CH2CH=CH2197.11g (488mmol) was dropped in 2 hours. It agitated at 110 degrees C after the end of dropping for 2 hours. Then, it lowered to 70 degrees C. NaOH solution 25.07g was added 0.1%, and it stirred for 2 hours. drying in 60 degrees C / 5KPa -- after the end of drying, and the temperature -- cull -- bora -- fin 3(made in Japanese Emba Illo Kem Carzou)2.51g was added, and it stirred for 2 hours. It filtered with the 0.1micrometer PTFE membrane filter, steam distillation of the filtrate was carried out using 100 degrees C / 5KPa, and the water 62.5g, and 206.3 g of object compounds (compound B1) were obtained (89% of yield).
88%	With sodium hydroxide; at 60 - 80℃; for 4h;Inert atmosphere;	800 g (2.2 mol) of FA-6 (manufactured by Unimartech) and 175.78 g (4.4 mol) of granular NaOH (manufactured by Wako Pure Chemical Industries, Ltd.) were added to a 2 L four-necked flask equipped with a thermometer and a cooling tube It was. Under a nitrogen atmosphere, while stirring at 200 rpm with a Teflon (registered trademark) 12 cm crescent stirring blade, the temperature was heated to 60 C. in the flask. 398.73 g (3.3 mol) of allyl bromide (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise thereto over 2 hours. After completion of the dropwise addition, the mixture was stirred at 70 C. for 1 hour and at 80 C. for 1 hour. Thereafter, the temperature was raised to 130 C. to remove excess allyl bromide. After cooling to 60 C., 800 g of ion-exchanged water was added, stirred for 30 minutes, then allowed to stand to separate the layers. The upper aqueous layer was withdrawn, 800 g of ion-exchanged water was added, and the mixture was stirred again, allowed to stand still and the aqueous layer was removed. Dehydrated at 60 C./5 KPa and distilled at 100 C./2 KPa to obtain 774.9 g of C 6 F 13 --CH 2 CH 2 --O - CH 2 CHCH 2 (yield 88%) as a fraction.
88%	With sodium hydroxide; at 60 - 80℃; for 4h;Inert atmosphere;	Into a 2 L four-necked flask equipped with a stirrer, a thermometer and a cooling tube,800 g (2.2 mol) of FA-6 (manufactured by Unimartech) and 175.78 g (4.4 mol) of granular NaOH (manufactured by Wako Pure Chemical Industries, Ltd.) were added. Under a nitrogen atmosphere, while stirring at 200 rpm with a Teflon (registered trademark) 12 cm crescent stirring blade, the temperature was heated to 60 C. in the flask.398.73 g (3.3 mol) of allyl bromide (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise thereto over 2 hours. After completion of the dropwise addition, the mixture was stirred at 70 C. for 1 hour and at 80 C. for 1 hour.Thereafter, the temperature was raised to 130 C. to remove excess allyl bromide.After cooling to 60 C., 800 g of ion-exchanged water was added, stirred for 30 minutes, then allowed to stand to separate the layers.The upper aqueous layer was withdrawn, 800 g of ion-exchanged water was added, and the mixture was stirred again, allowed to stand still and the aqueous layer was removed. Dehydrated at 60 C./5 KPa and distilled at 100 C./2 KPa to obtain 774.9 g of C 6 F 13 --CH 2 CH 2 --O - CH 2 CHCH 2 (yield 88%) as a fraction.
88%	With sodium hydroxide; at 60 - 80℃; for 4h;Inert atmosphere;	Into a 2 L four-necked flask equipped with a stirrer, a thermometer and a cooling tube,800 g (2.2 mol) of FA-6 (manufactured by Unimartech) and 175.78 g (4.4 mol) of granular NaOH (manufactured by Wako Pure Chemical Industries, Ltd.) were added.While stirring at 200 rpm with a Teflon (registered trademark) 12 cm crescent stirring blade under a nitrogen atmosphere,The temperature in the flask was brought to 60 C. with heating.398.73 g (3.3 mol) of allyl bromide (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise thereto over 2 hours.After completion of dropping, 1 hour at 70 C.,And the mixture was stirred at 80 C. for 1 hour.Thereafter, the temperature was raised to 130 C.,Excess allyl bromide was removed.After cooling to 60 C.,800 g of ion exchanged water was added,The mixture was stirred for 30 minutes, then allowed to stand to separate the layers.The upper aqueous layer was extracted,Further, 800 g of ion exchanged water was added,Agitation, standing, and removal of the water layer were performed again.Dehydrated at 60 C / 5 KPa,Distilled at 100 C / 2 KPa,As a fraction, 774.9 g of C6F13-CH 2CH 2-O-CH 2CH=CH2 was obtained (yield 88%).
88%	With sodium hydroxide; at 60 - 80℃; for 4h;Inert atmosphere;	nto a 2 L four-necked flask equipped with a stirrer, a thermometer and a cooling tube,800 g (2.2 mol) of FA-6 (manufactured by Unimartec Co., Ltd.)And 175.78 g (4.4 mol) of particulate NaOH (manufactured by Wako Pure Chemical Industries, Ltd.) were added. Under a nitrogen atmosphere, while stirring at 200 rpm with a Teflon (registered trademark) 12 cm crescent stirring blade, the temperature was heated to 60 C. in the flask.Allyl bromide (manufactured by Wako Pure Chemical Industries, Ltd.)39.8.73 g (3.3 mol) was added dropwise over 2 hours.After completion of dropping, 1 hour at 70 C.,And the mixture was stirred at 80 C. for 1 hour. Thereafter, the temperature was raised to 130 C. to remove excessive allyl bromide.After cooling to 60 C., 800 g of ion-exchanged water was added, stirred for 30 minutes, then allowed to stand to separate the layers.The upper aqueous layer was taken out, 800 g of ion exchanged water was added,Agitation, standing, and removal of the water layer were carried out again.Dehydrated at 60 C / 5 KPa, distilled at 100 C / 2 KPa,774.9 g of C6 F13-CH2CH2-O-CH2CH=CH2 was obtained (yield 88%).
88%	With sodium hydroxide; at 60 - 80℃; for 4h;Inert atmosphere;	To a 2 L four-necked flask equipped with a thermometer and a condenser, add 800 g (2.2 mol) of FA-6 (Unimatec) and 175.78 g (4.4 mol) of granular NaOH (Wako Pure Chemical Industries). It was.While stirring at 200 rpm with a 12 cm crescent stirring blade made of Teflon (registered trademark) in a nitrogen atmosphere, the temperature in the flask was adjusted to 60 C.Thereto, 398.73 g (3.3 mol) of allyl bromide (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise over 2 hours.After completion of dropping, the mixture was stirred at 70 C. for 1 hour and at 80 C. for 1 hour.Thereafter, the temperature was raised to 130 C. to remove excess allyl bromide.After cooling to 60 C., 800 g of ion-exchanged water was added, stirred for 30 minutes, and then allowed to stand to separate the layers.The upper aqueous layer was extracted, and 800 g of ion-exchanged water was further added, followed by stirring, standing still, and removal of the aqueous layer.Dehydrated at 60 C / 5KPa, distilled at 100 C / 2KPa,As a fraction, 774.9 g of C6F13-CH2CH2-O-CH2CH = CH2 was obtained (88% yield).
309.7 g	With sodium hydroxide; at 60 - 80℃; for 2.5h;	In a 5 L SUS 316 L four-neck separable flask (Apparatus A) equipped with a reflux condenser, a 200 mL dropping funnel and a turbine type stirring blade,(0.646 mol, viscosity nu: 2.5 × 10 -6 m 2 / s, density rhoL: 1680 kg / m 3) of 2- (perfluorohexyl) ethanol and stirred at 60 C. Next, 51.7 g (1 psi) of granular solid NaOH (Tosoh Pearl, Tosoh Corp., density rhos: 2130 kg / m 3, Deltarho: 450 kg / m 3) having a particle diameter of 0.7 mm was added while stirring was continued at 60 C. , And 117.3 g (0.970 mol) of allyl bromide was added dropwise over 30 minutes while maintaining at 60 C. (solid alkaline concentration X: 0.1438 kg / kg). The stirring speed during the reaction was 1.41 times the particle floating critical agitation speed njs calculated from the initial particle size of NaOH. After completion of the dropwise addition, the temperature was raised to 80 C. and stirring was continued for 2 hours. The apparent reaction rate after the reaction was analyzed by GC was 99.9%.(2) Washing processThereafter, 300.0 g of deionized water in the same amount as 2- (perfluorohexyl) ethanol was added, the mixture was stirred at 40 C. for 1 hour, and the mixture was allowed to stand for 2 hours to separate and extract the organic layer. Further, 180.0 g of deionized water which is 0.6 times the amount of 2- (perfluorohexyl) ethanol was added to the obtained organic layer, and the mixture was stirred at 40 C. for 1 hour and left to stand for 2 hours to give an organic layer Was separated and extracted. As a result of GC analysis of the obtained organic layer, the apparent reaction rate of allyl ((perfluorohexyl) ethyl) ether to 2- (perfluorohexyl) ethanol was 99.9%, and the apparent reaction ratio of 2- Difluorohexyl) ethanol was not confirmed.(3) Distillation processThereafter, excessive allyl bromide was distilled off under reduced pressure (120 C./26.7 kPa), and the product was distilled under reduced pressure (100 C./1.3 kPa) to obtain 309.7 g of a colorless purified product. Analysis of the obtained purified product by 1 H-NMR showed it to be allyl ((perfluorohexyl) ethyl) ether.[Apparent reaction rate measuring method]Wash the sample of the sampled reaction solution with the same amount of deionized water as the sample to obtain the lower organic phase. The organic phase obtained by performing this washing operation twice is diluted 100 times with methanol and measured by gas chromatography under the following conditions.

Reference： [1]Patent: JP6027883,2016,B2 .Location in patent: Paragraph 0037-0039
[2]Patent: JP6029378,2016,B2 .Location in patent: Paragraph 0080-0081
[3]Patent: JP2016/222599,2016,A .Location in patent: Paragraph 0044; 0045
[4]Patent: JP2017/25048,2017,A .Location in patent: Paragraph 0058-0059
[5]Patent: JP2017/95437,2017,A .Location in patent: Paragraph 0050
[6]Patent: JP2016/121094,2016,A .Location in patent: Paragraph 0047; 0048
[7]Patent: JP2016/8200,2016,A .Location in patent: Paragraph 0084-0085
[8]Patent: JP6301090,2018,B2 .Location in patent: Paragraph 0049; 0050
[9]Patent: JP6035121,2016,B2 .Location in patent: Paragraph 0050-0051
[10]Journal of Fluorine Chemistry,1987,vol. 35,p. 399 - 410
[11]Journal of Materials Chemistry,2000,vol. 10,p. 1765 - 1769
[12]RSC Advances,2015,vol. 5,p. 4547 - 4553
[13]Patent: JP6106022,2017,B2 .Location in patent: Paragraph 0048; 0049

6
[ 647-42-7 ]
[ 79-10-7 ]
[ 17527-29-6 ]

Yield	Reaction Conditions	Operation in experiment
88.8%	With toluene-4-sulfonic acid; hydroquinone; at 90℃; for 7h;Large scale; Green chemistry;	(3) In a 4-liter reactor equipped with electromagnetic stirring, a rectification column, a thermometer, a constant pressure dropping funnel, a separator, a condenser, etc., 2500 g of an intermediate product obtained by (2) (6.05 mol of a fluorine-containing alcohol) is added. 20 g of p-toluenesulfonic acid and 13 g of hydroquinone. StirThe temperature was raised to 90 C, and 413 g (5.74 mol) of acrylic acid was added dropwise thereto for 2 hours.At the end of the reaction, no significant water droplets were produced after 5 hours of continuous reaction.The fluorine-containing olefin and the unreacted fluoroalcohol are distilled off.Refining 2133 g of perfluorohexylethyl acrylate, the purity is 99.02%,The yield was 88.8%.
	With triethylamine; benzenesulfonyl chloride;Sumilizer GM; In tetrahydrofuran; at 20 - 40℃; for 1h;	Example 4In a 200-ml, three-necked glass reactor were placed 80 ml of tetrahydrofuran, 10 g (27.5 mmol) of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanol, 5 g (69 mmol) of acrylic acid, 10 g (57 mmol) of benzenesulfonic acid chloride and 0.1 g of a polymerization inhibitor, Sumilizer GM and allow to solve them. While the reaction temperature was kept at 40 C. or lower, 12 g (119 mmol) of triethylamine was added dropwise. After the completion of the dropwise addition, stirring was conducted at room temperature for 1 hour. At this point, the conversion was 99% and the selectivity was 99%.

Reference： [1]Patent: CN108911983,2018,A .Location in patent: Paragraph 0025
[2]Journal of Fluorine Chemistry,1988,vol. 38,p. 47 - 73
[3]Patent: US2009/23948,2009,A1 .Location in patent: Page/Page column 5

7
[ 647-42-7 ]
[ 53826-12-3 ]

Yield	Reaction Conditions	Operation in experiment
84%		To a solution of 1 /7,1 /7,2/7,2/7-perfluoro-1 -octanol (3.56 g, 3.78 mmol) in acetone (5 ml_) Jones reagent was added dropwise. The reaction was terminated when the solution turned solid yellow with simultaneous precipitation of green chromium salts. Then 2-propanol was added dropwise to reduce the excess oxidizing reagent. The blue solid was decanted, 50 ml_ water was added to the residue. The product was extracted with diethyl ether (4x 50 mL). The organic layers were combined and washed with water (50 mL), dried over MgS04 and concentrated under reduced pressure. The product was purified by recrystallization from CHCI3 to give white crystals 2/-/,2/-/-perfluorooctanoic acid 2p (3.10 g, yield = 84%). Spectral analysis: 1 H NMR (500 MHz, acetone-d6): delta = 3.41 (t, J = 18.5 Hz, 2H). 19F NMR (470 MHz, acetone-d6): delta = -81 .73 - -81 .85 (m, 3F), -1 12.36 - -122.74 (m, 2F), -122.34 - - 122.62 (m, 2F), -123.36 - -123.80 (m, 4F), -126.73 - -126.99 (m, 2F). 13C NMR (126 MHz, acetone-d6): delta = 164.36 (s), 35.90 (t, J = 22.0 Hz).

Reference： [1]Journal of Fluorine Chemistry,1995,vol. 70,p. 19 - 26
[2]Patent: WO2020/84599,2020,A2 .Location in patent: Page/Page column 16; 26; 27
[3]Tetrahedron,2009,vol. 65,p. 5271 - 5277
[4]Tetrahedron,2008,vol. 64,p. 522 - 528
[5]Tetrahedron Letters,2008,vol. 49,p. 6955 - 6958
[6]Journal of Fluorine Chemistry,2012,vol. 134,p. 115 - 121
[7]Journal of Molecular Liquids,2018,vol. 259,p. 239 - 248

8
[ 108-31-6 ]
[ 647-42-7 ]
bis(1H,1H,2H,2H-tridecafluoro-octyl)maleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In toluene; at 111℃; for 96h;	Maleic anhydride (0.63 g, 6.5 mmol),1H,1H,2H,2H-perfluoro-1-octanol (4.74 g, 13 mmol), p-toluenesulfonic acid monohydrate (p-TsOH) (0.19 g, 1.0 mmol) and toluene (50 mL) were added to a flask and heated to reflux for 96 hours at 111 C. The solution was separated and extracted with two washings of 5% sodium bicarbonate (50 mL each). The combined organic extracts were dried over anhydrous magnesium sulfate, and concentrated to remove the toluene at 140.30 mmHg (18.7 kPa) and 67 C.). The structure of the resulting liquid product di(1H,1H,2H,2H-perfluorooctyl) maleate (4.88 g, 93.4% yield, >80% purity) was confirmed by 1H NMR and LC/MS.

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2015,vol. 190,p. 1755 - 1763
[2]Journal of Fluorine Chemistry,1995,vol. 70,p. 187 - 192
[3]Patent: US2010/4478,2010,A1 .Location in patent: Page/Page column 14

9
[ 760-93-0 ]
[ 647-42-7 ]
[ 2144-53-8 ]

Reference： [1]Journal of Fluorine Chemistry,1997,vol. 82,p. 119 - 124

10
[ 647-42-7 ]
[ 920-46-7 ]
[ 2144-53-8 ]

Reference： [1]Chemical Communications,1997,p. 1811 - 1812

11
[ 647-42-7 ]
[ 98-59-9 ]
[ 51740-38-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine; In dichloromethane; at 0 - 20℃;	General procedure: A solution of TsCl (8.24212 mmol, 1 equiv) or MsCl (8.24 mmol, 1 equiv) in DCM (24 mL) was added dropwise to a stirred solution of fluorinated alcohol 1-5 (8.24 mmol, 1 equiv) and Et3N (1.78 mL, 1.55 equiv) at 0 C. After complete addition (10 min) the reaction mixture was allowed to reach rt and stirring was continued overnight. Then, the reaction mixture was washed with H2O (34 mL) and brine (34 mL). The organic layer was dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting crude product was crystallized from MeOH to afford 1a-5b.
92%	With triethylamine; In dichloromethane;	General procedure: Alcohol (8.74 g of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanol or 3.13 g of octanol, 24 mmol) and tertiary amine (30 mmol, triethylamine (4.2 ml) in the case of fluorinated alcohol and pyridine (2.4 ml) in the case of octanol) were dissolved in 50 ml of dichloromethane and p-toluenesulfonyl chloride (4.77 g, 25 mmol) was added in small portions. The reaction mixture was stirred overnight. The dichloromethane solution was then washed with water, dried over anhydrous MgSO4 and evaporated in vacuo. The crude product was crystallized from methanol in the case of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl tosylate. Crude octyl tosylate was used in the next step without further purification.
	With triethylamine; In butanone; at 37℃; for 15h;Inert atmosphere;	A 500 ml 4-necked flask was equipped with a heating mantle, an agitator shaft, a thermocouple, a reflux condenser, and a nitrogen inlet. The flask was charged with 55.2 grams of p-toluenesulfonyl chloride, 29.3 grams of trimethylamine and 170.0 grams of methyl ethyl ketone. The reaction mixture was stirred with a slight nitrogen purge in the headspace and 105.4 grams of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octanol was fed dropwise via a pressure equalizing addition funnel fitted to the top of the condenser, followed by an additional 55.0 grams of methyl ethyl ketone to rinse funnel and condenser into reaction flask. After exotherm to 37 C. subsided, the reaction mixture was stirred overnight, an additional 15 hours. The resulting mixture was filtered to remove the insoluble triethylamine hydrochloride salt and stripped to remove methyl ethyl ketone using a rotary evaporator. The final product was isolated in the form of 145.2 grams of a brown liquid containing the desired 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octyl p-toluenesulfonate, which crystallized upon cooling to ambient temperature.

Reference： [1]Arkivoc,2016,vol. 2017,p. 421 - 432
[2]Journal of Fluorine Chemistry,2014,vol. 164,p. 10 - 17
[3]Tetrahedron,2000,vol. 56,p. 3291 - 3301
[4]Journal of Fluorine Chemistry,2018,vol. 210,p. 70 - 77
[5]Tetrahedron Letters,2008,vol. 49,p. 6955 - 6958
[6]Tetrahedron,2009,vol. 65,p. 5271 - 5277
[7]Patent: US2018/334417,2018,A1 .Location in patent: Paragraph 0222

12
[ 358-23-6 ]
[ 647-42-7 ]
[ 78522-69-7 ]

Reference： [1]Synlett,2001,p. 685 - 687
[2]Tetrahedron,2002,vol. 58,p. 3841 - 3846
[3]Angewandte Chemie - International Edition,2012,vol. 51,p. 1849 - 1852
[4]Green Chemistry,2020,vol. 22,p. 2873 - 2878
[5]Synthetic Communications,2002,vol. 32,p. 3779 - 3790

13
[ 647-42-7 ]
[ 50-79-3 ]
3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2,5-dichlorobenzoate [ No CAS ]

Reference： [1]Macromolecules,2003,vol. 36,p. 2242 - 2247

14
[ 830330-63-7 ]
[ 4850-49-1 ]
[ 647-42-7 ]

Yield	Reaction Conditions	Operation in experiment
61%	With lithium triethylborohydride In tetrahydrofuran at 20℃; for 2h;

Reference： [1]Eames, Jason; Khanom, Hasina [Molecules, 2004, vol. 9, # 5, p. 266 - 277]

15
[ 112-54-9 ]
[ 647-42-7 ]
2-(perfluorohexyl)ethyl dodecyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	Pd-C; In hydrogen;	STR4 2-(Perfluorohexyl)ethanol 18.2 g (0.05 mol), 5% Pd-C (pH 7.2) 1.5 g as a catalyst were charged in a 70 ml autoclave equipped with a hydrogen gas inlet and a stirrer, to which was added dropwise dodecylaldehyde 13.8 g (0.075 mol) under atmospheric pressure over 6 hours and stirring was conducted at 105 C. for 8 hours while hydrogen was flowed continuously at 15 ml/min. After reaction was completed, the catalyst was removed by filtration, and an excess of dodecylaldehyde was removed under reduced pressure to provide the objective dodecyl{2-(perfluorohexyl)ethyl}ether 25.3 g (0.048 mol) as a colorless, transparent liquid. Isolation yield was 95%.

Reference： [1]Patent: US6002048,1999,A
[2]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 456 - 463

16
[ 647-42-7 ]
[ 353-50-4 ]
[ 375-85-9 ]
[ 56734-81-7 ]
[ 53826-12-3 ]

Reference： [1]Environmental Science and Technology,2004,vol. 38,p. 3316 - 3321

17
[ 2423-71-4 ]
[ 647-42-7 ]
[ 928790-01-6 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1315 - 1325

18
[ 21542-96-1 ]
[ 647-42-7 ]
[ 6609-64-9 ]
C₃₄H₅₉F₁₃NO₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	Stage #1: 1H,1H,2H,2H-tridecafluoro-n-octanol; 2-Chloro-2-oxo-1,3,2-dioxaphospholane With triethylamine In tetrahydrofuran; diethyl ether at 20℃; for 3h; Stage #2: N,N-dimethyldocosylamine In N,N-dimethyl-formamide at 20 - 70℃; for 72h;

Reference： [1]Peresypkin, Andrey; Clavel, Caroline; Menger, Fredric M. [Mendeleev Communications, 2007, vol. 17, # 2, p. 82 - 84]

19
1-iodo-1H,1H,2H,2H-perfluorohexadecane [ No CAS ]
[ 2043-55-2 ]
[ 2043-57-4 ]
[ 2043-53-0 ]
[ 2043-54-1 ]
[ 30046-31-2 ]
[ 60699-51-6 ]
[ 647-42-7 ]
[ 865-86-1 ]
[ 2043-47-2 ]
[ 39239-77-5 ]
[ 678-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	With water;silver nitrate; copper(II) sulfate; at 180℃;Gas phase;Conversion of starting material;	The catalyst of Preparation Example 8 (20 g) was placed in a stainless-steel reaction tube having an inner diameter of 10 mm and length of 250 mm, and was heated to 180° C. with a heater. CF3CF2 (CF2CF2)pCH2CH2I (mixture having a molar ratio of constituents of p=1/p=2/p=3/p=4/p=5/p=6=1.0/9.3/2.7/1.1/0.48/0.17) and water were introduced into a vaporizer at a rate of 2.8 g/hr and 12 g/hr, respectively, and were vaporized. Air was introduced into the reaction tube as a carrier gas at a rate of 35 cc/min. The vaporized gases were carried to the catalyst in the above reaction tube by the air to cause a catalytic reaction on the catalyst. Reaction products were recovered with an ice trap and a dry ice/methanol trap provided at the outlet of the reaction tube. The GC analysis of the products revealed that the corresponding alcohols were formed at the degree of conversion of 91percent and selectivity of 91percent.

Reference： [1]Patent: US6664430,2003,B1 .Location in patent: Page column 8-9

20
[ 2043-57-4 ]
[ 6900-35-2 ]
[ 647-42-7 ]
[ 25291-17-2 ]
[ 2144-53-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 10H-phenothiazine; In tert-butyl alcohol; at 130 - 170℃; for 6 - 9h;	Into a pressure resistant autoclave (10 liters) equipped with stirring vanes (Full Zone, manufactured by SHINKO PANTEC CO., LTD.), CqF2q+1(CH2)2I (wherein q is 4 or 6, hereinafter referred to as FI), potassium (meth)acrylate, phenothiazine (hereinafter referred to as PTZ) and tert-butanol (hereinafter referred to also as BuOH) were charged in the amounts (unit: mol) as shown in Table 1, and an ester-forming reaction was carried out under the reaction conditions shown in Table 1 to obtain a reaction mixture. The conversion and selectivity of the reaction are shown in Table 1.

Reference： [1]Patent: EP1486482,2004,A1 .Location in patent: Page 5; 6

21
[ 647-42-7 ]
[ 107-92-6 ]
[ 749228-47-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 2,2'-dipyridyldisulphide; triphenylphosphine; In benzene; at 80℃; for 24h;	Example 3 Typical procedure for a preparation of 7 by reverse fluorous solid phase extraction: Under argon atmosphere, 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol 6a (182 mg, 0.5 mmol), butyric acid (66 mg, 0.75 mmol), triphenylphospine (197 mg, 0.75 mmol) and Aldrithiol-2 (165 mg, 0.75 mmol) were dissolved in 5 mL of benzene. After stirring at 80 C. for 24 h, the reaction mixture was cooled, concentrated and charged to a column containing 6 g of standard silica gel. The column was eluted with 20 mL FC-72/diethylether (2/1), and the solvent was evaporated to provide the 7a (185 mg, 85%) as a colorless oil.

Reference： [1]Patent: US2005/283032,2005,A1 .Location in patent: Page/Page column 7

Yield	Reaction Conditions	Operation in experiment
	Purification / work up;	A mixture of 1H,1H,2H,2H-perfluoroalkan-1-ols, 4.5 g (Mixture 1, average MW=481, spiked with perfluorododecyl iodide), diethanolamine (1.7 wt. %), and water (11 wt. %), were charged in a 5-mL stainless steel shaker tube and heated to 200 C. for 4 hours. After the separation of aqueous phase, analysis was conducted according to Test Method 2. The level of perfluorododecyl iodide in the mixture of 1H,1H,2H,2H-perfluoroalkan-1-ols had decreased from 188 mg/kg to 3 mg/kg. Example 3 A mixture of 1H,1H,2H,2H-perfluoroalkan-1-ols, 280 g (Mixture 1, 0.582 mol, average MW=481), ethanolamine NH2CH2CH2OH (4.2 g, 0.069 mol, 1.5 wt. %), water (28 g, 10 wt. %), and isopropyl alcohol, MW=60 (14 g, 5 wt. %), were charged to a 400-mL stainless steel shaker tube, shaken and heated to 200 C. for 4 hours. Perfluorooctyl iodide (190 mg/kg), and perfluorooctanoic acid ester (80 mg/kg). After the separation of aqueous phase after the treatment, analyses were conducted according to Test Methods 1 and 2. The level of perfluorooctanoic acid had decreased from 100 mg/kg to 6 mg/kg. The level of perfluorooctyl iodide had decreased from 190 mg/kg to less than 2 mg/kg. The level of perfluorooctanoic acid ester had decreased from 80 mg/kg to less than 2 mg/kg. Example 4 A mixture of 1H,1H,2H,2H-perfluoroalkan-1-ols, 450 g (Mixture 1, 0.936 mol, average MW=481), ethanolamine (6.75 g, 1.5 wt. %), and water (45 g, 10 wt. %), were charged to a 400-mL stainless steel shaker tube, shaken and heated to 200 C. for 4 hours. After the separation of aqueous phase, analyses were conducted according to Test Methods 1 and 2. The level of perfluorooctanoic acid had decreased from 100 mg/kg to 4 mg/kg. The level of perfluorooctyl iodide had decreased from 190 mg/kg to less than 2 mg/kg. The level of perfluorooctanoic acid ester had decreased from 80 mg/kg to less than 2 mg/kg. Example 5 A mixture of 1H,1H,2H,2H-perfluoroalkan-1-ols, 4.17 g (Mixture 1, average MW=481), diethanolamine NH(CH2CH2OH)2 (0.09 g, 2.1 wt. %), water (0.2 g, 4.9 wt. %), were charged in a 5-mL stainless steel shaker tube and heated to 195 C. for 4 hours. After the separation of aqueous phase, analyses were conducted according to Test Methods 1 and 2. The level of perfluorooctanoic acid in the mixture of 1H,1H,2H,2H-perfluoroalkan-1-ols had decreased from 80 mg/kg to 4 mg/kg. The final level of C5F11COOH was 5-8 mg/kg, C6F13COOH was less than 4 mg/kg, C8F17COOH and C9F19COOH were below detection. The level of perfluorooctyl iodide had decreased from 90 mg/kg to less than 2 mg/kg. Examples 8-18 A mixture of 1H,1H,2H,2H-perfluoroalkan-1-ols, (3-5 g, Mixture 1, average MW=481 for Examples 8-18) combined with the additives in the amounts listed in Table 3 as weight percent of Mixture 1, were charged to a shaker tube and heated to the temperature designated in Table 3 for the time listed. After separation, analyses were conducted according to Test Methods 1 and 2. The starting and final levels of impurities were as listed in Table 3.

23
[ 647-42-7 ]
[ 108-10-1 ]
1,3-dimethylbutyl{2-(perfluorohexyl)ethyl}ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	Pd-C; In hydrogen;	STR2 2-(Perfluorohexyl)ethanol 18.2 g (0.05 mol), 4-methyl-2-pentanone 30.0 g (0.3 mol), 5% Pd-C (pH 7.2) 1.5 g as a catalyst were charged in a 70 ml autoclave equipped with a hydrogen gas inlet and a stirrer, and stirring was continued at 105 C. for 10 hours while continuously flowing hydrogen at 18 ml/min. under atmospheric pressure. After reaction was completed, catalyst was removed by filtration, and an excess of 4-methyl-2-pentanone was removed under reduced pressure. Further, after purification by silica gel column chromatography, the objective 1,3-dimethylbutyl{2-(perfluorohexyl)ethyl}ether 21.5 g (0.048 mol) was obtained as a colorless, transparent liquid. Isolation yield was 96%. 1 H-NMR(delta: ppm, CDCl3) 0.90 (overlapping of two doublets, 6H: a) 1.15 (doublet, 3H: b) 1.10~1.25 (complicated multiplet, 1H: c) 1.30~1.85 (complicated multiplet, 2H: d) 2.20~2.50 (complicated multiplet, 2H: e) 3.40~3.60 (complicated multiplet, 1H: f) 3.55~3.90 (complicated multiplet, 2H: g) b.p. 60~70 C./5Torr IR C--H stretching vibration:2926, 2878 cm-1 C--O--C stretching vibration:1083 cm-1 CF3 stretching vibration:1100~1340, 700~750 cm-1 CF2 stretching vibration:1146 cm-1

Reference： [1]Patent: US6060626,2000,A

24
[ 78385-26-9 ]
[ 647-42-7 ]
3-(3,3,4,4,5,5,6,6,7,7,8,8,8-TRIDECAFLUORO-OCTYLOXYMETHYL)-3-METHYLOXETANE [ No CAS ]
13-FOX 3-(3,3,4,4,5,5,6,6,7,7,8,8,8-TRIDECAFLUORO -OCTYLOXYMETHYL)-3-METHYLOXETANE [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In N-methyl-acetamide; mineral oil;	EXAMPLE B4 PREPARATION OF 13-FOX 3-(3,3,4,4,5,5,6,6,7,7,8,8,8-TRIDECAFLUORO -OCTYLOXYMETHYL)-3-METHYLOXETANE In a manner similar to that described above, 12.0 grams of <strong>[78385-26-9]3-bromomethyl-3-methyloxetane</strong> (73 mmol) was reacted with 26.5 grams of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-ol (72.7 mmol) in 300 milliliters of dimethylformamide in the presence of 3.9 grams of a 50 weight percent dispersion of sodium hydride (81 mmol) in mineral oil at 85 C. for 24 hours to give 21.5 grams (70% yield) of 3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyloxymethyl)-3-methyloxetane, a colorless oil with a boiling point of 66-68 C./2-2.5 mm-Hg; 1 H NMR (CDCl3) delta4.50 and 4.36 (AB, J=5.5 Hz, 4H), 3.78 (t, J=6.6 Hz, 2H), 3.53 (s, 2H), 2.42 (triplet of triplets, J=6.6 and 18 Hz, 2 H), and 1.31 (s, 3 H); 13 C NMR (CDCl3) delta79.89, 78.30, 63.31, 39.9, 31.64 (t), and 21.1 (signals due to carbons bearing fluorines are not included due to the complex splitting patterns and low peak intensities); 19 F NMR delta-81.4 (3F), -113.8 (2F), -118.2 (2F), -112.3 (2F), -124.1 (2F) and -126.7 (2F). The elemental analysis was: Calculated for C13 H13 F13 O2: C, 34.8; H, 2.9; F, 55.1. Found: C, 35.1; H, 3.0; F, 54.7.

Reference： [1]Patent: US5650483,1997,A

25
[ 78385-26-9 ]
[ 647-42-7 ]
3-(3,3,4,4,5,5,6,6,7,7,8,8,8-TRIDECAFLUORO-OCTYLOXYMETHYL)-3-METHYLOXETANE [ No CAS ]
13-FOX 3-(3,3,4,4,5,5,6,6,7,7,8,8,8-TRIDECAFLUORO-OCTYLOXYMETHYL)-3-METHYLOXETANE [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In N-methyl-acetamide; mineral oil;	EXAMPLE B4 PREPARATION OF 13-FOX 3-(3,3,4,4,5,5,6,6,7,7,8,8,8-TRIDECAFLUORO-OCTYLOXYMETHYL)-3-METHYLOXETANE In a manner similar to that described above, 12.0 grams of <strong>[78385-26-9]3-bromomethyl-3-methyloxetane</strong> (73 mmol) was reacted with 26.5 grams of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-ol (72.7 mmol) in 300 milliliters of dimethylformamide in the presence of 3.9 grams of a 50 weight percent dispersion of sodium hydride (81 mmol) in mineral oil at 85 C. for 24 hours to give 21.5 grams (70% yield) of 3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyloxymethyl)-3-methyloxetane, a colorless oil with a boiling point of 66-68 C./2-2.5 mm-Hg; 1 H NMR (CDCl3) delta 4.50 and 4.36 (AB, J=5.5 Hz, 4 H), 3.78 (t, J=6.6 Hz, 2 H), 3.53 (s, 2 H), 2.42 (triplet of triplets, J=6.6 and 18 Hz, 2 H), and 1.31 (s, 3 H); 13 C NMR (CDCl3) delta 79.89, 78.30, 63.31, 39.9, 31.64 (t), and 21.1 (signals due to carbons bearing fluorines are not included due to the complex splitting patterns and low peak intensities); 19 F NMR delta -81.4 (3 F), -113.8 (2 F), -118.2 (2 F), -112.3 (2 F), -124.1 (2 F) and -126.7 (2 F). The elemental analysis was: Calculated for C13 H13 F13 O2: C, 34.8; H, 2.9; F, 55.1. Found: C, 35.1; H, 3.0; F, 54.7.

Reference： [1]Patent: US5807977,1998,A

26
[ 647-42-7 ]
[ 609-23-4 ]
[ 124-63-0 ]
(2,4,6-triiodophenoxy)-1H,1H,2H,2H-perfluorooctane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium carbonate; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate; N,N-dimethyl-formamide	4 (2,4,6-Triiodophenoxy)-1H,1H,2H,2H-perfluorooctane STR7 EXAMPLE 4 (2,4,6-Triiodophenoxy)-1H,1H,2H,2H-perfluorooctane STR7 A mixture of 3.00 g (8.24 mmol) of 1H,1H,2H,2H-perfluorooctanol and 1.28 g (9.89 mmol) of N,N-diisopropylethylamine in 12 ml of dry dichloromethane was placed under nitrogen and cooled to 0° C. Methanesulfonyl chloride (1.04 g, 9.06 mmol) was added dropwise via syringe and the resulting solution was stirred at 0° C. for 1.5 hrs. The mixture was partitioned between 100 ml of dichloromethane and 100 ml of 1M HCl. The dichloromethane layer was then washed with water (100 ml) and brine (100 ml). The solution was dried over Na2 SO4 and concentrated in vacuo to afford 3.28 g (90%) of the mesylate as a white solid. A mixture of 2.11 g (4.77 mmol) of the above mesylate, 1.50 g (3.18 mmol) of 2,4,6-triiodophenol and 0.75 g (5.41 mmol) of potassium carbonate in 5 ml of dry DMF was stirred and heated to 80° C. under nitrogen for 40 hrs. The mixture was cooled and partitioned between 100 ml of ethyl acetate and 100 ml of 1M HCl. The ethyl acetate layer was then washed with water (50 ml) and brine (25 ml). The brown solution was dried over Na2 SO4 and concentrated in vacuo to yield a brown solid (1.89 g). The brown solid purified by flash chromatography (silica gel, hexanes) affording 1.35 g (52%) of the pure product. Mp: softens at 55°-58° C., melts at 63° C. Title Compound: 1 H (300 MHz) and 13 C (75 MHz) NMR spectra were consistent with the desired structure. FAB/MS; (M+1)+ 818. Calculated for C14 H6 F13 O3 O: C, 20.56; H, 0.74. Found: C, 20.75; H, 0.69.

Reference： [1]Current Patent Assignee: GENERAL ELECTRIC CO - US5607660, 1997, A

27
[ 2043-57-4 ]
[ 2043-53-0 ]
[ 2043-54-1 ]
[ 30046-31-2 ]
[ 10192-85-5 ]
[ 34395-24-9 ]
1H,1H,2H-perfluoro-1-tetradecene [ No CAS ]
[ 647-42-7 ]
[ 865-86-1 ]
[ 25291-17-2 ]
[ 21652-58-4 ]
[ 39239-77-5 ]
[ 678-39-7 ]
[ 30389-25-4 ]
[ 27905-45-9 ]
[ 17527-29-6 ]
[ 17741-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methoxy-phenol; hydroquinone; In tert-butyl alcohol; at 180 - 190℃; for 6h;Product distribution / selectivity;	(Example 1) A mixture of ethylene adducts of fluoroalkyl iodides each of which adduct was represented by CF3(CF2)nCH2CH2I was obtained as a mixture containing the adducts of n≤6 in an amount of 5 mol%, the adduct of n=7 in an amount of 76 mol%, the adduct of n=8 in an amount of 0 mol%, the adduct of n=9 in an amount of 17 mol% and the adduct of n≥10 in an amount of 2 mol%. Next this mixture was reacted with an acrylic acid compound to give a mixture containing the fluorine-containing acrylic esters represented by the formula (1). Specifically, 1576g (2.67 mol) of the ethylene adducts of the fluoroalkyl iodides, 320g (2.90 mol) of potassium acrylate, 680mL of tert-butyl alcohol, and 1.8g of hydroquinone and 0.32g of hydroquinone monomethylether as inhibitors of polymerization were firstly charged into an autoclave with a volume of 3L and heated to 180C to 190C and reacted for 6 hours. After the reaction, a reaction mixture was cooled. Next, KI as a byproduct was removed by filtration. Thereafter, a filtrate was subjected to distillation to remove tert-butyl alcohol and then 1288g of a reaction mixture having a composition shown in Table 1 was obtained. 1000g of this reaction mixture was measured and charged into a still and then subjected to distillation for 2 hours at a pressure in a rectifier of 0.9kPa and a still temperature of 160C, introducing air into the still at a flow rate of 20 ml/min such that the oxygen concentration in the distillation column was 1 mol% relative to the total moles of gas-phase components in the distillation column. Further, the continuous distillation was carried out using an oldershaw-type distillation column with 20 plates which was made of glass as a whole (including the internal structure). As a result of the distillation, 886g of a mixture after distillation having a composition as shown in Table 1 was obtained as a distillate liquid (a recovery rate based on the fluorine-containing acrylic esters was 97%). In Table 1, the compositions of the reaction mixture and the mixture after distillation were determined by gas chromatography. Table 1 Component Reaction mixture (mol%) Mixture after distillation (mol%)C6F13CH=CH2 0.91 NDC8F17CH=CH2 13.65 NDC10F21CH=CH2 3.09 NDC12F25CH=CH2 0.34 0.01C6F13CH2CH2OH 0.11 NDC8F17CH2CH2OH 1.57 NDC10F21CH2CH2OH 0.35 0.04C12F25CH2CH2OH 0.04 0.05C6F13CH2CH2OCOCH=CH2 4.09 5.1C8F17CH2CH2OCOCH=CH2 60.73 75.93C10F21CH2CH2OCOCH=CH2 13.54 16.92C12F25CH2CH2OCOCH=CH2 1.58 1.96 As shown in Table 1, of the impurities contained in the reaction mixture, particularly C8F17CH=CH2, C10F21CH=CH2, C8F17CH2CH2OH and C10F21CH2CH2OH were able to be removed considerably by the distillation. As a result, the highly-pure mixture of the fluorine-containing acrylic esters was obtained, in which the contents of the fluorine-containing acrylic esters of n=7 and n=9 contained were large. Specifically, the mixture contained, as the impurities, C10F21CH2CH2OH (n=9) in an amount of 0.04 mol%, C12F25CH=CH2 (n=11) in an amount of 0.01 mol% and C12F25CH2CH2OH (n=11) in an amount of 0.05 mol%. (Comparative Example 1) The mixture of the fluorine-containing acrylic esters was obtained similarly to Example 1, and then the distillation was carried out similarly to Example 1. However, the distillation was carried out under the nitrogen atmosphere without using the inhibitor of polymerization and introducing oxygen into the distillation column. As a result, the esters were polymerized in the distillation column, and the intended mixture with a less impurity content was not able to be obtained well. It is considered that this was related also to the fact that the still temperature was made high in order that the ester with a large "n" value (n=7) was intended to be obtained by the distillation.

Reference： [1]Patent: EP1757578,2007,A1 .Location in patent: Page/Page column 6-7; 8-9

28
[ 110-53-2 ]
[ 647-42-7 ]
[ 1193009-93-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium hydroxide; In 1-methyl-pyrrolidin-2-one; water; at 50 - 70℃; for 7h;	The same fluoroalkyloxy alkanes as in Examples 1- 4 were prepared following an alternative procedure. A mixture comprising 0.1 moles of fluorinated alcohol, 60 ml of N-methyl-2-pyrrolidone, 0.2 moles of 1- bromoalkane, and 60 ml of a 45% aqueous solution of KOH was heated under stirring for 5 hours at 500C, then at 700C for 2 hours so as to complete the reac- tion. The raw reaction mixture was filtered so as to remove the formed KBr, and then diluted in 20 ml of water; the organic phase thus obtained comprised the desired fluoroalkyloxy alkane (yield: 80%) .
72%		To a mixture, kept under stirring, of C6F13CH2CH2OH(252 g, 0.692 moles), tetrahydrofurane (350 ml) and cyclohexane (300 ml) at 250C, an aqueous solution ofNaOH (400 ml, 50%) was added drop-wise. After stirring for 2 hours, benzyltriethyl ammonium chloride (25 g, 0.11 moles) as phase transfer catalyst, and then 1- bromopentane (209 g, 1.38 moles) were added. The reaction mixture was kept under stirring at 400C for 40 hours, then at 700C for 8 hours. The resulting mixture was poured into water and the organic phase thus ob- tained was washed two times with water. After removing the fraction having a low boiling point, the raw product was subjected to distillation at reduced pressure, thus obtaining 215 g of C6F13CH2CH2O (CH2) 4CH3 (yield 72%, boiling point 110C/6 mbar, n 1.3385) . Spectrographic data confirm the obtained structure: GC/MS m/z at 435 (M+H)+, 377 (M-CH2CH2CH2CH3) +, 71 (- CH2CH2CH2CH2CH3) + ; for NMR data see Tables 1-2.

Reference： [1]Patent: WO2009/133575,2009,A1 .Location in patent: Page/Page column 14
[2]Patent: WO2009/133575,2009,A1 .Location in patent: Page/Page column 11
[3]Journal of Fluorine Chemistry,2010,vol. 131,p. 844 - 851

29
[ 647-42-7 ]
[ 106-94-5 ]
[ 1193010-01-3 ]

Yield	Reaction Conditions	Operation in experiment
71%		To a mixture, kept under stirring, of C6F13CH2CH2OH (252 g, 0.687 moles), tetrahydrofurane (350 ml) and cyclohexane (300 ml) at 250C, an aqueous solution of NaOH (400 ml, 50%) was added drop-wise. After stirring for- 2 hours, benzyltriethyl ammonium chloride (25 g, 0.11 moles) as phase transfer catalyst, and then 1- bromopropane (170 g, 1.38 moles) were added. The reaction mixture was kept under stirring at 400C for 40 hours, then at 700C for 8 hours. The resulting mixture was poured into water and the organic phase thus obtained was washed two times with water. After removing the fraction having a low boiling point, the raw product was treated with toluene 2, 4-diisocyanate, in order to remove unreacted fluorinated alcohol, and then subjected to distillation at reduced pressure, thus obtaining 200 g of C6F13CH2CH2O (CH2) 2CH3 (yield 71%, boiling point 1740C, n 1.3245) . Spectrographic data confirm the obtained structure: GC/MS m/z at 405 (M- H)+, 377 (M-CH2CH3)4", 73 ( -CH2OCH2CH2CH3) +, 43 (- CH2CH2CH3) +; for NMR data see Tables 1-2.

Reference： [1]Patent: WO2009/133575,2009,A1 .Location in patent: Page/Page column 11-12
[2]Journal of Fluorine Chemistry,2010,vol. 131,p. 844 - 851

30
[ 647-42-7 ]
[ 51595-55-2 ]
[ 1251034-31-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: 1H,1H,2H,2H-tridecafluoro-n-octanol With potassium In diethyl ether at 20℃; Inert atmosphere; Stage #2: 4,4'-dinitro-2,2'-bipyridyl-N,N'-dioxide at 100℃; for 32h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Hirose, Takuji; Shigaki, Shuhei; Hirose, Makoto; Fushimi, Atsushi [Journal of Fluorine Chemistry, 2010, vol. 131, # 9, p. 915 - 921]

31
[ 116-14-3 ]
[ 74-85-1 ]
[ 354-64-3 ]
[ 10192-85-5 ]
[ 34395-24-9 ]
1H,1H,2H-perfluoro-1-tetradecene [ No CAS ]
[ 647-42-7 ]
[ 865-86-1 ]
[ 25291-17-2 ]
[ 21652-58-4 ]
[ 39239-77-5 ]
[ 678-39-7 ]
[ 30389-25-4 ]
[ 27905-45-9 ]
[ 17527-29-6 ]
[ 17741-60-5 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of fluoroalkyl alcohols represented by C2F5(CF2CF2)nI was produced as follows. 100g of CF3CF2I as a telogen was charged into a reactor together with 10g of a copper catalyst. These are stirred to give a slurry in which the copper catalyst was suspended and the slurry was heated to 80C. Tetrafluoroethylene as a taxogen was charged into the reactor with the temperature inside the reactor kept at 80C and the reaction pressure was maintained at 0.8MPa. At the time when 10g of tetrafluoroethylene was charged, it was confirmed by gas chromatography that the telomerization reaction proceeded. The resultant mixture of the fluoroalkyl iodides was subjected to distillation selecting the theoretical number of ten(10), the bottom temperature of from 60C to 140C and the pressure in the column of from 100 to 10kPa. The telomers with smaller "n" values were withdrawn from the column top sequentially and then a mixture containing the fluoroalkyl iodides of n=3 and n=4 in an amount of 91 mol% in total was drawn from the column top and this mixture was used in the next ethylene addition step. More specifically, this mixture contained the fluoroalkyl iodides with n≤2 in an amount of 5 mol%, one with n=3 in an amount of 76 mol%, one with n=4 in an amount of 17 mol% and one with n≥5 in an amount of 2 mol%. The mixture obtained in this manner was subjected to ethylene addition to give ethylene adducts. The ethylene addition step was carried out as follows. 100g of the fluoroalkyl iodide mixture and 5g of copper catalyst as a catalyst were charged into an autoclave and then heated to 100C. Next, an ethylene gas was charged into a gas phase so that the reaction pressure was kept at 0.3MPa, and the reaction was made for three hours. As a result, a mixture of the ethylene adducts was obtained. An yield of the ethylene adducts was 99 mass%. Next, an esterification step was carried out according to the following procedures. 1576g (2.67 mol) of the mixture of the ethylene adducts obtained by carrying out the ethylene addition step according to the above procedures, 320g (2.90 mol) of potassium acrylate, 680mL of tert-butyl alcohol, and 1.8g of hydroquinone and 0.32g of hydroquinone monomethylether were firstly charged into an autoclave with a volume of 3L and heated to 180C-190C and reacted for 6 hours. After the reaction, a reaction mixture was cooled. Next, KI as a byproduct was removed by filtration. Thereafter, a filtrate was subjected to distillation to remove tert-butyl alcohol and then a reaction mixture having a composition shown in Table 1 was obtained. 1000g of this reaction mixture was measured and charged into a still and then subjected to distillation using a rectifier with theoretical plate number of ten(10) and selecting the pressure inside the rectifier of 0.9kPa and the still temperature of 160C. As a result, a mixture after distillation having a composition as shown in Table 1 was obtained as a distillate liquid In Table 1, the compositions of the reaction mixture and the mixture after distillation were determined by gas chromatography; As shown in Table 1, the impurities contained in the reaction mixture, specifically, C8F17CH=CH2, C10F21CH=CH2, C8F17CH2CH2OH and C10F21CH2CH2OH were able to be removed considerably by the distillation. As a result, the highly-pure mixture of the fluorine-containing acrylic esters was obtained, in which the contents of the fluorine-containing acrylic esters of n=3 and n=4 contained were large. Specifically, the mixture contained, as the impurities, C10F21CH2CH2OH (n=4) in an amount of 0.04 mol%, C12F25CH=CH2 (n=5) in an amount of 0.01 mol% and C12F25CH2CH2OH (n=5) in an amount of 0.05 mol%

Reference： [1]Patent: EP1757574,2007,A1 .Location in patent: Page/Page column 8-9

32
[ 784-14-5 ]
[ 647-42-7 ]
[ 1262852-80-1 ]

Yield	Reaction Conditions	Operation in experiment
38%	Stage #1: 1H,1H,2H,2H-tridecafluoro-n-octanol With sodium hydride In tetrahydrofuran; mineral oil at 20 - 40℃; Inert atmosphere; Stage #2: 2,3,4,5,6-pentafluorobiphenyl In tetrahydrofuran; mineral oil Inert atmosphere; regioselective reaction;

Reference： [1]Location in patent: experimental part Kvíčala, Jaroslav; Beneš, Michal; Paleta, Oldřich; Král, Vladimír [Journal of Fluorine Chemistry, 2010, vol. 131, # 12, p. 1327 - 1337]

33
[ 1667-10-3 ]
[ 647-42-7 ]
[ 1260518-65-7 ]
[ 1260518-66-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; water; for 2.5h;	Preparation of 4-((1H, lH,2H,2H-perfluoro- 1 -octyl)oxymethyl)-4 ' -chloromethylbiphenylCF 113XUH '25WC1H '25OHA boiling solution of 40.0 g (0.1 mol) lH,lH,2H,2H-perfluoro-l-octanol and 25.1 g (0.1 mol) <strong>[1667-10-3]4,4'-bis(chloromethyl)biphenyl</strong> in 150 mL TEtaF was treated dropwise over 1 hr with 8.0 g 50% NaOEta/water. The reaction was stopped at 2.5 hr and quenched in water and extracted with methylene chloride. This material (61.5 g) was a pale yellow solid with some liquid, CeFi3C2H4OH by GLC. Trituration with hexane left 19.3 g solid, shown by GLC to be 55% dichloride plus two new products. The hexane was evaporated to 36.4 g. Trituration with perfluoromethylmorpholine left 26.4 g solid. GC/MS showed the major component (74%) to be the desired 4-(( IH, lH,2H,2H-perfiuoro- 1 -octyl)oxymethyl)-4 ' - chloromethylbiphenyl with the diether (4, 4'-bis((lH,lH,2H,2H-perfluoro-l- octyl)oxymethyl)biphenyl as minor component.
	With sodium hydroxide; In tetrahydrofuran; water; for 3.5h;	Example 10 Preparation of 1 -oct l)oxymethyl)-4' -chloromethylbiphenyl A boiling solution of 40.0 g (0.1 mol) lH,lH,2H,2H-perfluoro-l-octanol and 25.1 g (0.1 mol) <strong>[1667-10-3]4,4'-bis(chloromethyl)biphenyl</strong> in 150 mL THF was treated dropwise over 1 hr with 8.0 g 50% NaOH/water. The reaction was stopped at 2.5 hr and quenched in water and extracted with methylene chloride. This material (61.5 g) was a pale yellow solid with some liquid, C6F13C2H4OH by GLC. Trituration with hexane left 19.3 g solid, shown by GLC to be 55% dichloride plus two new products. The hexane was evaporated to 36.4 g. Trituration with perfluoromethylmorpholine left 26.4 g solid. GC/MS showed the major component (74%) to be the desired 4-((lH, lH,2H,2H-perfluoro-l-octyl)oxymethyl)-4'- chloromethylbiphenyl with the diether (4, 4'-bis((lH, lH,2H,2H-perfluoro-l- octyl)oxymethyl)biphenyl as minor component.

Reference： [1]Patent: WO2011/5396,2011,A1 .Location in patent: Page/Page column 33
[2]Patent: WO2011/87717,2011,A1 .Location in patent: Page/Page column 22

34
[ 647-42-7 ]
[ 106-96-7 ]
[ 1334419-24-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydroxide; In tetrahydrofuran; at 20℃;Cooling with ice;	General procedure: A dry flask was charged with THF (9 mL), NaOH pellets (0.48 g, 12 mmol), and perfluorohexylethanol or perfluoroheptylmethanol (3 mmol). The flask was immersed in an ice-bath and the contents stirred for 10 min. Propargyl bromide (0.54 g, 4.5 mmol) was added dropwise and the reaction mixture stirred and gradually allowed to warm to r.t. over 24 h. The reaction mixture was poured into Et2O (20 mL) and water (50 mL), the layers separated and the aqueous layer extracted with more Et2O (3 × 20 mL). The combined organic extracts were washed with 10% HCl soln. followed by sat. aq. NaHCO3 and brine, and then dried over Na2SO4. Column chromatography (silica gel, Et2O/LP, 10:90) followed by Kulgelrohr distillation gave the desired products.

Reference： [1]Journal of Fluorine Chemistry,2011,vol. 132,p. 898 - 906
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2015,vol. 190,p. 1755 - 1763
[3]Organic Process Research and Development,2018,vol. 22,p. 1509 - 1517
[4]Synlett,2013,vol. 24,p. 1093 - 1096
[5]Journal of Fluorine Chemistry,2016,vol. 191,p. 1 - 13

35
[ 647-42-7 ]
[ 4049-33-6 ]
[ 1356839-61-6 ]

Yield	Reaction Conditions	Operation in experiment
34%	With boron trifluoride diethyl etherate; In dichloromethane; at 20℃;Cooling with ice;	1,2,3,4-Tetra-O-acetyl-β-d-xylopyranose (2) (662 mg, 2.08 mmol) and 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanol (544 μL, 909 mg, 2.49 mmol, 1.2 equiv) were dissolved in CH2Cl2 (8 mL) at room temperature. The stirring solution was cooled in an ice-water bath. BF3·Et2O (385 μL, 443 mg, 3.12 mmol, 1.5 equiv) was added drop wise. The ice-bath was removed and the solution was allowed to warm to room temperature overnight. The reaction was quenched with satd NaHCO3 (10 mL). After separation of the layers the aqueous phase was extracted twice with CH2Cl2 (15 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel flash column chromatography using hexanes-EtOAc as eluent (5:1, v/v) to yield 10 (434 mg, 34%) as a white solid. Rf 0.75 (4:1 hexanes: EtOAc, v/v); mp 94-95 C; 1H NMR (CDCl3, 400 MHz): δ 2.04 (s, 3H, CH3CO), 2.04 (s, 3H, CH3CO), 2.06 (s, 3H, CH3CO), 2.42 (tt, 2H, J2',3' = 18.8 Hz, J1',2' = 6.5 Hz, H-2'), 3.40 (dd, 1H, J5a,5b = 11.8, J4,5a = 8.6 Hz, 5a), 3.79 (dt, 1H, J1'a,1'b = 10.4 Hz, J1'a,2' = 6.7 Hz, H-1'a), 4.07-4.16 (m, 2H, H-1'b and H-5e), 4.52 (d, 1H, J1,2 = 6.6 Hz, H-1), 4.90-4.97 (m, 2H, H2 and H4), 5.16 (pseudo t, 1H, J2,3 = J3,4 = 8.3 Hz, H-3); 13C NMR (CDCl3, 100 MHz,): δ 20.5, 20.6, 20.7, 31.4, 61.3, 62.0, 68.7, 70.3, 71.0, 100.6, 169.4, 169.8, 170.0; 19F NMR (282 MHz, CDCl3): δ -81.3 (CF3), -113.9 (CF2), -122.4 (CF2), -123.3 (CF2), -124.1 (CF2), -126.6 (CF2); HRESIMS m/z: calcd for C19H19O8F13Na [M+Na]+: 645.0765; found: 645.0781; Anal. Calc for C19H19O8F13: C 37.67; H 3.08; found: C 36.75; H 2.96.

Reference： [1]Carbohydrate Research,2012,vol. 349,p. 12 - 23

36
[ 108-05-4 ]
[ 647-42-7 ]
1,1,2,2 tetrahydroperfluoro octanylvinyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate; In toluene; at 100℃; for 3h;Inert atmosphere;	General procedure: A two-necked, 500-mL round bottom flask was equipped with a magnetic stirring bar and a three-way stopcock, of which one way was connected to an argon flow line and the other was connected to a vacuum line. The apparatus was flame-dried in vacuum, and allowed to cool to room temperature under an argon purge. To a solution of [IrCl(cod)]2 (1 mol%) in dry toluene triethylene glycol monomethyl ether, vinyl acetate (2.0 equiv), and Na2CO3 (0.60 equiv) were added and the mixture was stirred at 100 C for 3 h. After the reaction, the resulting salts were removed and washed with Et2O. The solvent was removed under reduced pressure. Purification of the residue by vacuum distillation (2 times distillation with CaH2) gave the product.

Reference： [1]Tetrahedron,2012,vol. 68,p. 3243 - 3252

37
[ 876-08-4 ]
[ 647-42-7 ]
[ 1293408-03-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; In acetone; at 10 - 20℃; for 2h;Inert atmosphere;	Into a reactor (internal capacity: 300 mL, made of glass) equipped with a stirrer and a dropping funnel, linear C6F13CH2CH2OH (45.9 g), triethylamine (15.3 g) and acetone (100 mL) were put and stirred. Then, by an ice bath, the inner temperature of the reactor was adjusted to be at most 10C, and in a nitrogen atmosphere, a solution of 4-(chloromethyl)benzoic acid chloride (25.0 g) in acetone (20 mL) was dropwise added. Further, the temperature was returned to room temperature, and stirring was continued for 2 hours. The obtained reaction crude liquid was transferred to a separating funnel, dichloropentafluoropropane (tradename: AK-225, manufactured by Asahi Glass Company, Limited) (200 mL) was added, followed by washing three times with distilled water (200 mL), and the solvent in the AK-225 phase was distilled off to obtain 65.0 g of a compound (C-1) (white solid) represented by the following structural formula (C-1) and classified into the above compound (C). The yield was 95%.
95%	With triethylamine; In acetone; at 10 - 20℃; for 2h;Inert atmosphere;	Into a reactor (internal capacity: 300 mL, made of glass) equipped with a stirrer and a dropping funnel, linear C6F13CH2CH2OH (48.2 g), triethylamine (16.1 g), and acetone (100 mL) were put and stirred. Then, by an ice bath, the inner temperature of the reactor was adjusted to be at most 10 C., and in a nitrogen atmosphere, a solution of 4-(chloromethyl)benzoic acid chloride (25.0 g) in acetone (20 mL) was dropwise added. Further, the temperature was returned to room temperature, and stirring was continued for 2 hours. (0126) The obtained reaction crude liquid was transferred to a separating funnel, dichloropentafluoropropane (tradename: AK-225, manufactured by Asahi Glass Company, Limited, hereinafter sometimes referred to as AK-225) (100 mL) was added, followed by washing three times with distilled water (100 mL), and the solvent in the AK-225 phase was distilled off to obtain 66.6 g of a compound (A-1) (white solid) represented by the following structural formula (A-1) and classified into the above compound (A). The yield was 95%. The measured results of 1H-NMR of the obtained compound (A-1) are shown below. Here, each measured value means a measured value derived from a group shown in ( ) following the measured value, but in a case where this group has a portion defined by [ ], the measured value means a measured value derived from the portion defined by [ ]. Hereinafter, the same applies to all of the measured results of NMR shown in Examples. 1H-NMR (solvent:CDCl3) delta(ppm): 2.62 (2H, m, -CH2CF2-), 4.62 (2H, s, ClCH2-), 4.64 (2H, t, -OCH2-), 7.48 (2H, d, Ph), 8.03 (2H, d, Ph). Into a reactor (internal capacity: 100 mL, made of glass) equipped with a stirrer and a dropping funnel, acrylic acid (2.00 g), potassium carbonate (4.60 g) and DMF (20 mL) were put and stirred. Then, heating was carried out so that the inner temperature of the reactor became 50 C., and a solution of the compound (A-1) (14.3 g) in DMF (10 mL) was dropwise added. The dropping funnel was replaced by a Dimroth condenser, and the reactor was heated to 80 C., followed by stirring for 2 hours. (0131) The obtained reaction crude liquid was transferred to a separating funnel, AK-225 (50 mL) was added, followed by washing three times with distilled water (50 mL), and the solvent in the AK-225 phase was distilled off to obtain 14.8 g of the fluorinated compound (I-1) of the present invention (white solid) represented by the following formula (I-1). The yield was 95%. (0132) (0133) The measured results of 1H-NMR of the obtained fluorinated compound (1-1) of the present invention are shown below. (0134) 1H-NMR (solvent:CDCl3) delta(ppm): 2.62 (2H, m, -CH2CF2-), 4.64 (2H, t, -COO[CH2]CH2-), 5.26 (2H, s, -COO[CH2]Ph-), 5.90 (1H, d, transC?CH2), 6.19 (1H, dd, -CH?), 6.48 (1H, d, cisC?CH2), 7.46 (2H, d, Ph), 8.04 (2H, d, Ph).

Reference： [1]Patent: EP2497763,2012,A1 .Location in patent: Page/Page column 14
[2]Patent: US8471056,2013,B2 .Location in patent: Page/Page column 15; 16

38
[ 647-42-7 ]
[ 99-96-7 ]
[ 255041-11-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With toluene-4-sulfonic acid; at 140℃; for 6h;	Example 1Into a reactor (internal capacity: 500 mL, made of glass) equipped with a stirrer, 4-hydroxybenzoic acid (135.0 g), 4-toluenesulfonic acid monohydrate (9.30 g) and C6F13CH2CH2OH (533.8 g) were put and stirred. Then, heating was carried out so that the internal temperature of the reactor became 140 C., and stirring was further continued for 6 hours while the pressure in the reactor was reduced (from 0 to -0.05 MPa) to distilled off water. The internal temperature of the reactor was decreased to 110 C., and the pressure was further reduced to distill off the excess C6F13CH2CH2OH.The obtained white solid was dissolved in 900 mL of ethyl acetate and put in a separating funnel, followed by washing twice with deionized water (1,200 mL), and the solvent in the ethyl acetate phase was distilled off to obtain 460.8 g of the following compound (A-1) (white solid). The yield was 98%. The measurement results of 1H-NMR of the obtained compound (A-1) are shown below. Here, each measured value means a measured value derived from a group shown in ( ) following the measured value, but in a case where this group has a portion defined by [ ], the measured value means a measured value derived from the portion defined by [ ]. Hereinafter, the same applies to all of the measurement results of NMR shown in Examples.1H-NMR (solvent: CD3COCD3) delta (ppm): 2.81 (2H, m, -CH2CF2-), 4.62 (2H, t, -COO[CH2]CH2-), 6.94 (2H, d, Ph), 7.91 (2H, d, Ph), 9.21 (1H, s, -OH)I

Reference： [1]Patent: US2013/5924,2013,A1 .Location in patent: Page/Page column 5-6

39
[ 647-42-7 ]
[ 99-76-3 ]
[ 255041-11-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With toluene-4-sulfonic acid; at 120℃; for 6h;Inert atmosphere;	Into a reactor (internal capacity: 200 mL, made of glass) equipped with a stirrer, in a nitrogen atmosphere, methyl 4-hydroxybenzoate (25.0 g), 4-toluenesulfonic acid monohydrate (3.13 g) and linear C6F13CH2CH2OH (119.7 g) were put and stirred. Then, heating was carried out so that the inner temperature of the reactor became 120 C., the reactor was depressurized (from 0 to -0.05 MPa), and stirring was continued for 6 hours while distilling methanol off. Further, by lowering the depressurizing degree, excess C6F13CH2CH2OH was distilled off. The obtained white solid was recrystallized from chloroform to obtain 71.5 g of a compound (B-1) (white solid) represented by the following structural formula (B-1) and classified into the above compound (B). The yield was 90%. The measured results of 1H-NMR of the obtained compound (B-1) are shown below. (0144) 1H-NMR (solvent:CD3COCD3) delta(ppm): 2.81 (2H, m, -CH2CF2-), 4.62 (2H, t, -COO[CH2]CH2-), 6.94 (2H, d, Ph), 7.91 (2H, d, Ph), 9.21 (1H, s, -OH). (0145) Into a reactor (internal capacity: 50 mL, made of glass) equipped with a stirrer and a dropping funnel, the compound (B-1) (10.0 g), triethylamine (2.51 g) and methylene chloride (20 mL) were put and stirred. Then, by an ice bath, the inner temperature of the reactor was adjusted to be at most 10 C., and in a nitrogen atmosphere, acrylic acid chloride (2.15 g) was dropwise added. Further, the temperature was returned to room temperature, and stirring was continued for 2 hours. (0146) The obtained reaction crude liquid was transferred to a separating funnel, AK-225 (50 mL) was added, followed by washing three time with distilled water (20 mL), and the solvent in the AK-225 phase was distilled off to obtain 8.35 g of a fluorinated compound (I-3) of the present invention (white solid) represented by the following structural formula (I-3). The yield was 75%. The measured results of 1H-NMR of the obtained fluorinated compound (I-3) of the present invention are shown below. (0149) 1H-NMR (solvent:CDCl3) delta(ppm): 2.61 (2H, m, -CH2CF2-), 4.63 (2H, t, -COOCH2-), 6.06 (1H, s, transC?CH2), 6.33 (1H, dd, -CH?), 6.63 (1H, s, cisC?CH2), 7.24 (2H, d, Ph), 8.09 (2H, d, Ph).

Reference： [1]Patent: US8471056,2013,B2 .Location in patent: Page/Page column 16; 17

40
[ 647-42-7 ]
[ 103-72-0 ]
O-[2-perfluorohexylethyl] N-phenylthiocarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		To a solution of the perfluoroalkyl alcohol (10 mmol) in 10 mLof dry THF, was added sodium hydride (60% 1.4 equiv. dissolved in 2 mL of dry THF in oil) at 0 C under nitrogen atmosphere. The mixture was stirred for 30 min. Then 1.35 g (10 mmol) of henylisothiocyanate was added. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. The mixture was quenched with saturated aqueous ammonium chloride. The aqueous layer was washed with diethyl ether and the combined organic layers were dried over Na2SO4. The solvent was removed by vacuum evaporation and the crude products were purified with column chromatography on silica gel (70-230 meshes) using petroleum ether/diethyl ether (8:2) as eluent or recrystallized in cyclohexane to give the corresponding O-perfluoroalkyl thiocarbamate.

Reference： [1]Journal of Fluorine Chemistry,2013,vol. 156,p. 101 - 105
[2]Synthetic Communications,2017,vol. 47,p. 15 - 21

41
[ 647-42-7 ]
[ 622-78-6 ]
O-[2-perfluorohexylethyl] N-benzylthiocarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		To a solution of the perfluoroalkyl alcohol (10 mmol) in 10 mLof dry THF, was added sodium hydride (60% 1.4 equiv. dissolved in 2 mL of dry THF in oil) at 0 C under nitrogen atmosphere. The mixture was stirred for 30 min. Then 1.35 g (10 mmol) of henylisothiocyanate was added. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. The mixture was quenched with saturated aqueous ammonium chloride. The aqueous layer was washed with diethyl ether and the combined organic layers were dried over Na2SO4. The solvent was removed by vacuum evaporation and the crude products were purified with column chromatography on silica gel (70-230 meshes) using petroleum ether/diethyl ether (8:2) as eluent or recrystallized in cyclohexane to give the corresponding O-perfluoroalkyl thiocarbamate.

Reference： [1]Journal of Fluorine Chemistry,2013,vol. 156,p. 101 - 105
[2]Synthetic Communications,2017,vol. 47,p. 15 - 21

42
[ 542-85-8 ]
[ 647-42-7 ]
O-[2-perfluorohexyl] N-ethylthiocarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		To a solution of the perfluoroalkyl alcohol (10 mmol) in 10 mLof dry THF, was added sodium hydride (60% 1.4 equiv. dissolved in 2 mL of dry THF in oil) at 0 C under nitrogen atmosphere. The mixture was stirred for 30 min. Then 1.35 g (10 mmol) of henylisothiocyanate was added. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. The mixture was quenched with saturated aqueous ammonium chloride. The aqueous layer was washed with diethyl ether and the combined organic layers were dried over Na2SO4. The solvent was removed by vacuum evaporation and the crude products were purified with column chromatography on silica gel (70-230 meshes) using petroleum ether/diethyl ether (8:2) as eluent or recrystallized in cyclohexane to give the corresponding O-perfluoroalkyl thiocarbamate.

Reference： [1]Journal of Fluorine Chemistry,2013,vol. 156,p. 101 - 105
[2]Synthetic Communications,2017,vol. 47,p. 15 - 21

43
[ 647-42-7 ]
[ 57-06-7 ]
O-[2-perfluorohexylethyl] N-allylthiocarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		To a solution of the perfluoroalkyl alcohol (10 mmol) in 10 mLof dry THF, was added sodium hydride (60% 1.4 equiv. dissolved in 2 mL of dry THF in oil) at 0 C under nitrogen atmosphere. The mixture was stirred for 30 min. Then 1.35 g (10 mmol) of henylisothiocyanate was added. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. The mixture was quenched with saturated aqueous ammonium chloride. The aqueous layer was washed with diethyl ether and the combined organic layers were dried over Na2SO4. The solvent was removed by vacuum evaporation and the crude products were purified with column chromatography on silica gel (70-230 meshes) using petroleum ether/diethyl ether (8:2) as eluent or recrystallized in cyclohexane to give the corresponding O-perfluoroalkyl thiocarbamate.

Reference： [1]Journal of Fluorine Chemistry,2013,vol. 156,p. 101 - 105

44
[ 3724-19-4 ]
[ 647-42-7 ]
1H,1H,2H,2H-perfluorooctyl-3-(pyridin-3-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 336h;
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

Reference： [1]Cabrera, Silvia; Navas, Francisco; Matesanz, Ana I.; Maroto, Marta; Riedel, Tina; Dyson, Paul J.; Quiroga, Adoracion G. [Inorganic Chemistry, 2019, vol. 58, # 11, p. 7200 - 7208]
[2]Clavel, Catherine M.; Paunescu, Emilia; Nowak-Sliwinska, Patrycja; Dyson, Paul J. [Chemical Science, 2014, vol. 5, # 3, p. 1097 - 1101]

45
[ 355-43-1 ]
[ 109-92-2 ]
[ 647-42-7 ]

Yield	Reaction Conditions	Operation in experiment
		The reactor was charged with 0.25 g of 5% Ru/C, 1.0 g of a mixture of C6F13CH2CHO and C6F13CH2CH(OH)(OEt), 5 mL of THF, and 5 mL ofdilute H2SO4 (pH =2.2). The hydrogenation was conducted at 80 Cand 3.1 MPa for 3.5 h. GC analysis showed nearly quantitative formationof the desired alcohol C6F13CH2CH2OH and only traces of otherfluorinated products or products resulting from reaction of the THFsolvent.

Reference： [1]Journal of Fluorine Chemistry,2017,vol. 201,p. 7 - 10

46
[ 355-43-1 ]
[ 109-92-2 ]
[ 647-42-7 ]
[ 210896-77-8 ]

Yield	Reaction Conditions	Operation in experiment
74%Chromat.; 23%Chromat.		The hydrogenation reactor was charged with 0.5 g of Ru/C catalyst and 15.0 g of a mixture of C6F13CH2CHO and C6F13CH2CH(OH)(OEt) inTHF. The reactor was brought to 80 C and 2.1 MPa. After 3.5 h the reaction was halted and the reaction analyzed by GC and GCMS which showed quantitative conversion to a mixture of alcohol C6F13CH2CH2OH (74%), ether C6F13CH2CH2OEt (23%), and acetal C6F13CH2CH(OEt)2 (3%).

Reference： [1]Journal of Fluorine Chemistry,2017,vol. 201,p. 7 - 10

47
[ 647-42-7 ]
[ 252237-40-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triphenylphosphine; bromine / acetonitrile / 5 h / 60 °C / Inert atmosphere 2: 4 h / 150 °C 3: hydrogen bromide / 4 h / 120 °C

Reference： [1]Lukáč, Miloš; Garajová, Mária; Mrva, Martin; Devínsky, Ferdinand; Ondriska, František; Kubincová, Janka [Journal of Fluorine Chemistry, 2014, vol. 164, p. 10 - 17]

48
[ 647-42-7 ]
1-bromo-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With bromine; triphenylphosphine; In acetonitrile; at 60℃; for 5h;Inert atmosphere;	3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctane-1-ol (20 g,55 mmol) and triphenylphosphine (15.7 g, 60 mmol) were dissolved in 110 ml of anhydrous acetonitrile and deoxygenated with argon. The mixture was heated at 60 C and bromine (9.6 g,60 mmol) was added dropwise. The mixture was stirred for 5 h at this temperature. After cooling down to room temperature, the reaction mixture was extracted with diethyl ether and the ether layers were washed with brine. After drying with Na2SO4, the ether was evaporated and the crude product was dissolved in 100 ml of dichloromethane. This solution was stirred with 50 g of silica gel for 2 h and then filtered and evaporated. The crude product was distilled at reduced pressure.

Reference： [1]Journal of Fluorine Chemistry,2014,vol. 164,p. 10 - 17

49
[ 647-42-7 ]
[ 4981-83-3 ]
[ 1401243-56-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1H,1H,2H,2H-tridecafluoro-n-octanol; 2-(Benzyloxy)ethyl p-toluenesulfonate With N-benzyl-trimethylammonium hydroxide In water; toluene at 70℃; for 0.5h; Stage #2: With potassium hydroxide In water; toluene at 80℃; for 5h;	3.3.2 (3-2) Synthesis of Fluoroalkyl Ether (3c) Tosyl derivative (3b; 16.2 g, 50 mmol) and 2-(perfluorohexyl)ethanol (12.1 ml, 55 ml) were added to 100 ml of toluene, and a benzyltrimethylammonium hydroxide aqueous solution (105 ml) was added thereto. After heating the mixture to 70°C and stirring the mixture for 30 min, a potassium hydroxide aqueous solution (3.1 g/water 20 ml) was added. The mixture was heated to 80°C, and a reaction was allowed for 5 hours. After adding ethyl acetate (100 ml) and water (50 ml) for separation, the resulting liquid was concentrated to obtain ether (3c) as a crude product. The product was directly used as raw material in the next step without being purified. 1HNMR (300 MHz, CDCl3) δ 2.5 (m, 2H), 3.8 (d, 2H), 4.0 (d, 2H), 4.4 (s, 2H), 7.1-7.4 (m, 5H)
	Stage #1: 1H,1H,2H,2H-tridecafluoro-n-octanol; 2-(Benzyloxy)ethyl p-toluenesulfonate With N-benzyl-trimethylammonium hydroxide In water; toluene at 70℃; for 0.5h; Stage #2: With potassium hydroxide In water; toluene at 80℃; for 5h;	1-2 Synthesis of 1-2) fluorinated alkyl ether (1c) of100ml of toluene was added to the tosyl derivative (1b)(16.2g, 50mmol) and 2- (perfluorohexyl) ethanol(12.1ml, 55ml), was added benzyltrimethylammonium hydroxideaqueous ammonium 105ml. After the temperature was raised to 70 deg.] C andstirred for 30 minutes, adding an aqueous solution of potassium hydroxide (3.1g/ water 20ml). Temperature was then raised to 80 , thereaction for 5 hours. JoinEthyl acetate 100ml, 50ml water, followed by liquidseparation, then concentrated. Ether to give a crude product (. 1C). Withoutpurification, the product was used as a raw material for the next step.

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - EP2738155, 2014, A1 Location in patent: Paragraph 0070
[2]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - CN104159996, 2016, B Location in patent: Paragraph 0236; 0240; 0241; 0242

50
[ 108-30-5 ]
[ 647-42-7 ]
[ 125111-32-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine; In tetrahydrofuran; at 100℃; for 1h;	A succinic anhydride (9.7 g, 49 mmol), tetrahydrofuran (10 ml), and triethylamine (0.2 mL) were added to <strong>[647-42-7]2-(perfluorohexyl)ethanol</strong> (33.3 g, 46 mmol). A reaction was allowed for 60 min at an increased temperature of 100C while stirring the mixture. Water (100 mL) was added after cooling the mixture to 30C, and the precipitated crystals formed upon further cooling to 15C were filtered off to obtain carboxylic acid (5a; 39.7 g, 94%).
94%	In tetrahydrofuran; at 100℃; for 1h;	To a mixture of <strong>[647-42-7]2-(perfluorohexyl)ethanol</strong> (33.3 g, 46 mmol) and succinic anhydride (9.7 g, 49 mmol) and 10ml tetrahydrofuranand stirred at 100C And allowed to react for 60 minutes.Thereafter, the mixture was cooled to 30 DEG C, 100 mL of water was added, and the mixture was further cooled to 15 DEG C, and the precipitated crystals were collected by filtration to obtain carboxylic acid (1-2a). (39.7 g, 94%).
	With triethylamine; N-ethyl-N,N-diisopropylamine;	Ways carboxylic acid (3d) can be synthesized by a known method, using the above shown illustrated by a compound (3c) was synthesized. In addition, the use of thionyl chloride to the carboxylic acid (3d) to the acid chloride derivative, gallic acid and so hydrate obtained by reacting a carboxylic acid (3e). The use of thionyl chloride acid (. 3E) to the acid chloride derivative, in the presence of DIPEA diol (3d) obtained by reacting the compound (24).

With pyridine; In 1,2-dimethoxyethane; at 65 - 75℃; for 36h;Inert atmosphere;

Weigh 2.2 g of succinic anhydride in a 250 ml dry anhydrous three-necked flask.After filling with nitrogen for 10 min, the air in the flask and a small amount of water in the reaction system were replaced.80 ml of anhydrous ethylene glycol dimethyl ether was added to the reaction system.After pyridine 0.15ml, the temperature was raised to 75 C, 7.28 g of trifluoro-n-octanol and 40 ml of ethylene glycol dimethyl ether were gradually added dropwise to the reaction system, and the addition process was carried out to ensure that the temperature of the reaction system was controlled at 65-75 C, and the addition was completed. Rear,The reaction was maintained at 75 C for 18 h, and the reaction was stopped after 18 h.After the reaction, a certain amount of saturated NaHCO3 was added to the reaction system, and the succinic acid monoester acid was converted into a sodium salt dissolved in water. Then, a certain amount of ethyl acetate is poured into the reaction system, and unreacted fluoroalcohol, succinic anhydride and the reaction to form a succinic acid diester are dissolved in the organic phase, and the monoester acid is dissolved in the aqueous phase, and the aqueous phase is separated.The obtained aqueous phase is placed in an ice water bath, acidified with concentrated hydrochloric acid, and extracted with a certain amount of ethyl acetate, and the extract is dried with a certain amount of anhydrous magnesium sulfate.Distillation under reduced pressure gave a purer succinic acid monoester acid. The synthetic route is as follows:

Reference： [1]Patent: EP2738155,2014,A1 .Location in patent: Paragraph 0078-0080
[2]Patent: KR101634475,2016,B1 .Location in patent: Paragraph 0310-0313; 0318
[3]Patent: CN104159996,2016,B .Location in patent: Paragraph 0271; 0274; 0275
[4]Patent: CN108997182,2018,A .Location in patent: Paragraph 0060; 0061; 0062; 0063; 0064; 0066

51
[ 1663-39-4 ]
[ 647-42-7 ]
[ 1420072-98-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tetrabutylammomium bromide; potassium hydroxide; In water; toluene; at 20℃; for 3h;Cooling with ice;	[0087] 2-(Perfluorohexyl)ethanol (18.2 g, 50 mmol) was added to toluene, and potassium hydroxide (3.5 g)/water (3.5 ml) was added to the mixture. Under ice-cooled condition, acrylic acid tert-butyl ester (10.3 ml, 70 mmol) and tetrabutylammonium bromide (1.61 g, 5 mmol) were added, and the mixture was stirred at room temperature for 3 hours. The reaction was quenched by addition of dilute hydrochloric acid. The mixture was separated in an ethyl acetate/water system, and the resulting liquid was concentrated with a rotary evaporator. After column purification, purified ester (7b; 19.0 g, yield 77%) was obtained.

Reference： [1]Patent: EP2738155,2014,A1 .Location in patent: Paragraph 0085-0087

52
[ 647-42-7 ]
(R)-2-[4-(octyloxy)phenyl]-4,5-dihydrothiazole-4-carboxylic acid [ No CAS ]
(R)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 4,5-dihydro-2-[4-(octyloxy)phenyl]thiazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h;Inert atmosphere;	General procedure: To a stirred solution of the corresponding thiazoline 4a-c (2.0 mmol) in dry CH2Cl2 (8 mL) under N2 atmosphere at room temperature, were added subsequently the corresponding alcohol (2.0 mmol) EDCI (2.0 mmol) and catalytic amount of DMAP. After 16 h, the organic phase was transferred to an extraction funnel, washed with saturated NaHCO3 (2 × 10 mL), water (2 × 10 mL) and the organic layer was dried with Na2SO4. The solvent was evaporated and the remaining product was purified by chromatography (hexanes/AcOEt = 80:20).

Reference： [1]Journal of the Brazilian Chemical Society,2014,vol. 25,p. 1493 - 1503

53
[ 647-42-7 ]
C₂₄H₂₉NO₃S [ No CAS ]
C₃₂H₃₂F₁₃NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h;Inert atmosphere;	General procedure: To a stirred solution of the corresponding thiazoline 4a-c (2.0 mmol) in dry CH2Cl2 (8 mL) under N2 atmosphere at room temperature, were added subsequently the corresponding alcohol (2.0 mmol) EDCI (2.0 mmol) and catalytic amount of DMAP. After 16 h, the organic phase was transferred to an extraction funnel, washed with saturated NaHCO3 (2 × 10 mL), water (2 × 10 mL) and the organic layer was dried with Na2SO4. The solvent was evaporated and the remaining product was purified by chromatography (hexanes/AcOEt = 80:20).

Reference： [1]Journal of the Brazilian Chemical Society,2014,vol. 25,p. 1493 - 1503

54
[ 1196463-67-8 ]
[ 647-42-7 ]
C₁₈H₁₁BrF₁₃NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h;Inert atmosphere;	General procedure: To a stirred solution of the corresponding thiazoline 4a-c (2.0 mmol) in dry CH2Cl2 (8 mL) under N2 atmosphere at room temperature, were added subsequently the corresponding alcohol (2.0 mmol) EDCI (2.0 mmol) and catalytic amount of DMAP. After 16 h, the organic phase was transferred to an extraction funnel, washed with saturated NaHCO3 (2 × 10 mL), water (2 × 10 mL) and the organic layer was dried with Na2SO4. The solvent was evaporated and the remaining product was purified by chromatography (hexanes/AcOEt = 80:20).

Reference： [1]Journal of the Brazilian Chemical Society,2014,vol. 25,p. 1493 - 1503

55
[ 647-42-7 ]
2-chloro-6-allyloxy-s-tetrazine [ No CAS ]
2-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-oxy)-6-allyloxy-s-tetrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With 2,4,6-trimethyl-pyridine; In dichloromethane; at 100℃; for 24h;Sealed tube;	General procedure: Allyloxy-chloro-tetrazine 1 (1 mmol) and fluorinated alcohol (1 mmol) were mixed in 10 mL of anhydrous dichloromethane. 2,4,6-collidine (1 mmol) was added dropwise into the solution and the mixture was heated to 100 C in a pressure tube for 24 h with stirring. After cooling to r.t, the solvent was removed by evaporation and the residue was passed through a column chromatography (Silica gel, 2/8 dichloromethane/petroleum ether) to give F-alkylethoxyallyloxy -1,2,4,5-tetrazine as a pink fluorescent solid.

Reference： [1]Dyes and Pigments,2014,vol. 108,p. 64 - 69

56
[ 647-42-7 ]
[ 106131-61-7 ]
2-chloro-6-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-oxy)-s-tetrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With 2,4,6-trimethyl-pyridine; In dichloromethane; at 20℃; for 12.0h;Inert atmosphere;	General procedure: Dichloro-s-tetrazine (1 mmol) and fluorinated alcohol (1 mmol) were dissolved in anhydrous dichloromethane (10 mL). 2,4,6-collidine (1 mmol) was added dropwise at room temperature in the solution, and the mixture was stirred for 12 h under N2 atmosphere.The solvent was evaporated and the residue was passed through a column of silica (2/8 dichloromethane/petroleum ether v/v) to give compound 2 as a pink solid, with a ?yellow? fluorescence on TLC (using a standard laboratory UV lamp with a broad band centred at 365 nm).

Reference： [1]Dyes and Pigments,2014,vol. 108,p. 64 - 69

57
[ 647-42-7 ]
C₈H₆F₁₃O₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.7%	With phosphorus pentoxide; phosphoric acid; In water; at 50 - 60℃; for 48h;	Into a 500 ml three-necked flask equipped with a stirrer, 32.7 g (225.7 mmol) of phosphorus pentoxide, 1,1,1,2,2,3,3,4,4, 118.7 g of 5,5,6,6-tridecafluorooctane and 23.2 g of 85% by mass phosphoric acid (100.5 mmol as phosphorus pentoxide, 495.1 mmol as water) were added and stirred for 10 minutes Later, 118.7 g (326.2 mmol) of perfluorohexylethyl alcohol was added. The temperature of the oil bath was raised to 50 C., and the mixture was reacted under stirring at the same temperature for 24 hours. Subsequently, the temperature of the oil bath was raised to 60 C. and reacted under stirring at the same temperature for 24 hours, then the solvent was removed, 150 g of ethyl acetate was newly added and dissolved. The same amount of water was added thereto, and washing with water was carried out with stirring, and the operation of removing used water was carried out a total of three times. Thereafter, the solvent was removed and dried to obtain 145 g of a white powdery product. 93.5 mol% of the perfluoroalkyl group-containing phosphoric monoester in the product thus obtained, 4.6 mol% of the perfluoroalkyl group-containing phosphate diester, 1.9 mol% of the phosphoric acid, Met. These were calculated using 31 P NMR. The calculation method of each numerical value is as follows. For convenience, a perfluoroalkyl group-containing phosphate monoester is referred to as a monoester, and a perfluoroalkyl group-containing phosphate diester is abbreviated as gels.Monoester = monoester / (monoester + diester + phosphoric acid)Diester = diester / (monoester + diester + phosphoric acid)Phosphoric acid = phosphoric acid / (monoester + diester + phosphoric acid) Further, the amount of unreacted perfluorohexylethyl alcohol was 0.6 mol%. This was calculated using 1H NMR.The calculation method is as follows. For convenience, perfluorohexylethyl alcohol is abbreviated as Rf alcohol. The other abbreviations are as described above.Rf alcohol = Rf alcohol / (Rf alcohol + monoester + diester) Note that the yield of the perfluoroalkyl group-containing phosphate monoester in the product was 94.7% and the selectivity was 95.3 mol% . The calculation method of each numerical value is as follows. Abbreviations of the names of the respective components are as described above.Selectivity = monoester / (monoester + diester)Reaction Rate = 100 - Rf AlcoholYield = selectivity × reaction rate

Reference： [1]Patent: JP2015/71552,2015,A .Location in patent: Paragraph 0036-0039; 0040

58
C₂₄H₁₂BF₃₉ [ No CAS ]
[ 647-42-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With dihydrogen peroxide; sodium hydroxide; In water; at 45℃; for 2h;	(2) To the reaction intermediate was added 40 mL of 3 mol / L sodium hydroxide and 16 mL of a 37% aqueous solution of hydrogen peroxide,The reaction was carried out at 45 C for 2 hours. After completion of the reaction, the solvent was distilled off at 40 C,After washing with deionized water three times, after liquid separation, drying with anhydrous magnesium sulfate to produce perfluoroalkyl ethanol;9.93 g of perfluorohexyl ethanol was obtained in a yield of 91%.

Reference： [1]Patent: CN105732328,2016,A .Location in patent: Paragraph 0026; 0028; 0029

59
[ 647-42-7 ]
[ 124-63-0 ]
[ 156575-40-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In dichloromethane; at 0 - 20℃;	General procedure: A solution of TsCl (8.24212 mmol, 1 equiv) or MsCl (8.24 mmol, 1 equiv) in DCM (24 mL) was added dropwise to a stirred solution of fluorinated alcohol 1-5 (8.24 mmol, 1 equiv) and Et3N (1.78 mL, 1.55 equiv) at 0 C. After complete addition (10 min) the reaction mixture was allowed to reach rt and stirring was continued overnight. Then, the reaction mixture was washed with H2O (34 mL) and brine (34 mL). The organic layer was dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting crude product was crystallized from MeOH to afford 1a-5b.

Reference： [1]Arkivoc,2016,vol. 2017,p. 421 - 432

60
[ 647-42-7 ]
[ 106-89-8 ]
1,3-bis[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)oxy]-2-propanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium hydroxide; In water; at 45℃; for 10h;	1, 2g (5.49mmol) 1H, 1H, 2H, 2H- perfluorooctanol, 304mg (0.82mmol) of tetrabutylammonium iodide, 0.21 mL (2.75 mmol) of epichlorohydrin was added in a round bottom flask was added 18mol / L 11 mL of aqueous sodium hydroxide solution, stirred for 10 hours at 45 , detecting the end of the reaction by thin layer chromatography.After the reaction was cooled to room temperature, the reaction solution was poured into deionized water and extracted with ether, the organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated and column chromatography, to give compound 2-1, which in 60% yield.

Reference： [1]Patent: CN104355972,2016,B .Location in patent: Paragraph 0035-0038

61
[ 647-42-7 ]
[ 68499-56-9 ]
C₂₂H₂₃ClF₁₃NO₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 24h;Inert atmosphere;	To a stirred solution of 1,3,4,6-tetra-O-acetyl-2-chloroacetamido-2-deoxy-beta-d-glucopyranose 19 (0.091 g, 0.214 mmol)in anhydrous DCM (4.3 mL) under an argon atmosphereand room temperature BF3·Et2O (0.06 mL, 0.428 mmol)and 1,1,1,2,2,3,3,4,4,5,5-pentadecauorooctanol 17 (0.076 g,0.214 mmol) were added and stirred for 24 h. The reaction mixture was diluted with EtOAc (3 mL) and washed with aq. sat.NaHCO3 (3 mL). The organic phase was dried over Na2SO4and concentrated in vacuo. The crude product was purifedby column chromatography (EtOAc/CH 1:1, v/v) gave 21 as awhite solid. Yield: (0.106 g) 69%; 1H NMR (300 MHz, CDCl3)delta 6.65 (d, J = 8.6 Hz, 1H, NH), 5.40 (dd, J = 10.5 Hz, J =9.3 Hz, 1H, H-3), 5.09 (t, J = 9.6 Hz, 1H, H-4), 4.83 (d, J =8.2 Hz, 1H, H-1), 4.29 (dd, J = 12.3 Hz, J = 4.9 Hz, 1H, H-6a), 4.21-4.12 (m, 2H, H-6b, H-2), 4.00 (d, J = 2.7 Hz, 2H,CH2Cl), 3.91-3.82 (m, 2H, OCH2CH2(CF2)5CF3), 3.77 (ddd,J = 9.9 Hz, J = 4.9 Hz, J = 2.4 Hz, 1H, H-5), 2.53-2.37 (m,2H, CH2(CF2)5CF3), 2.11 (s, 3H, OAc), 2.05 (s, 3H, OAc), 2.06(s, 3H, OAc); 13C NMR (101 MHz, CDCl3) delta 170.60 C(O)CH3,170.58 C(O)CH3, 169.4 C(O)CH3, 166.4 C(O)CH2Cl, 121.7-106.4 (m, (CF2)5CF3), 100.4 C-1, 72.0 C-5, 71.4 C-3, 68.4 C-4, 61.9 C-6, OCH2CH2(CF2)5CF3, 55.0 C-2, 42.3 CH2Cl,31.3 (t, J = 21.5 Hz, OCH2CH2(CF2)5CF3), 20.63 C(O)CH3,20.60 C(O)CH3, 20.55 C(O)CH3; 19F NMR (377 MHz, CDCl3)delta -80.77, -113.39, -121.89, -122.86, -123.53, -126.12;MS (ESI) m/z [M+H]+ calcd for C22H24ClF13NO9: 728.0932;found: 728.0930; m/z [M+Na]+ calcd for C22H23ClF13NNaO9:750.0751; found: 750.0748.

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2017,vol. 192,p. 683 - 694

62
[ 647-42-7 ]
[ 106-89-8 ]
1,3-bis[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)oxy]-2-propanol [ No CAS ]
C₃₀H₂₃F₃₉O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%; 14%	With tetra-(n-butyl)ammonium iodide; sodium hydroxide; In water; at 45℃;	To a mixture of 1,1,2,2-tetrahydroperfluorooctanol (2.00 g, 5.49 mmoL) and TBAI (0.61 mg, 1.65 mmoL) in a 50 mL flask was added aqueous NaOH (8 mol/L, 5.5 mL) and epichlorohydrin (0.65 mL, 8.23 mmoL). The mixture was stirred at 45 C overnight, and then poured into H2O and extracted with Et2O, the organic layer was dried over MgSO4, concentrated and purified by silica gel chromatography (EtOAc/petroleum ether, 1/5, v/v) to give 2 (1.15 g, 1.47 mmol, 53%) and 5 (0.31 g, 0.26 mmol, 14%) both as clear oil. Compound 2: IR (KBr, cm-1): v 3310, 2890, 1482, 1404, 1362, 1241, 1141. 1H NMR (400 MHz, CDCl3): delta 4.03-3.84 (m, 1H), 3.87-3.71 (m, 4H), 3.60-3.45 (m, 4H), 2.50-2.30 (m, 5H, including 2.34 (d, 1H)). 13C NMR (100 MHz, CDCl3): delta 71.9, 69.2, 63.3 (t), 31.4 (t). HRMS (ESI) m/z Calcd. for C19H14F26O3Na: 807.0425 [M+Na]+, found: 807.0417. Compound 5: IR (KBr, cm-1): v 3433, 2921, 2882, 1384, 1237, 1132. 1H NMR (400 MHz, CDCl3): delta 4.10-3.76 (m, 5H), 3.76-3.58 (m, 6H), 3.58-3.23 (m, 6H), 2.94 (d, 1H, J = 4.2 Hz), 2.56-2.24 (m, 6H). 13C NMR (100 MHz, CDCl3): delta 78.6, 72.0, 71.9, 71.0, 70.9, 69.6, 63.4-63.3 (m), 31.4 (t). HRMS (ESI) m/z Calcd. for C30H23F39O5Na: 1227.0820 [M+Na]+, found: 1227.0830.

Reference： [1]Chinese Chemical Letters,2017,vol. 28,p. 1693 - 1700

63
[ 93-04-9 ]
[ 647-42-7 ]
2-[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)oxy]naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With bismuth(lll) trifluoromethanesulfonate; In water; 1,2-dichloro-ethane; at 110℃; for 24h;Schlenk technique; Inert atmosphere;	General procedure: A flame dried Schlenk flask was charged with Bi(OTf)3 (13.1 mg,0.020 mmol), alkyl aryl ethers (0.40 mmol), alcohols or thiols (1.2 mmol) andCH2ClCH2Cl (0.20 mL), and then the resulting mixture was stirred at 110 C (or 130 C forthe synthesis of 1m) for 24 h. The solvent was removed under the reduced pressure, andthe residue was subjected to flash column chromatography on silica gel with hexane /AcOEt as eluents to afford the corresponding aryl ethers or aryl thioethers

Reference： [1]Chemistry Letters,2018,vol. 47,p. 927 - 930

64
[ 647-42-7 ]
N^α-(tert-butyloxycarbonyl)-(R)-lysine tert-butyl ester [ No CAS ]
C₂₄H₃₃F₁₃N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		The corresponding fluoroalcoholic substrate 1e (0.728 g, 2.0 mmol) was added to the reaction flask and anhydrous DMF (3 mL) was added.Additional DSC (0.613 g, 1.2 eq.) and pyridine (0.16 mL, 1.0 eq.).The mixture was heated at 40 C for 15 h.It was monitored by TLC until the alcohol was completely reacted. Cool the mixture to room temperature,Boc-t-Bu-lysine (0.604 g, 2.0 mmol) was added.Keep the temperature below 30 C.The reaction mixture was then stirred at room temperature overnight.It was monitored by TLC until the starting material was complete.Water (10 mL) and ethyl acetate (10 mL) were added to the mixture.The organic layer was separated and the aqueous layer was evaporated elutCombine the two organic layers, using 1 mol/L hydrochloric acid in sequence.Wash with water and saturated brine,It was dried over anhydrous magnesium sulfate. Concentrate the organic solution,Fluorine-containing amino acid derivative precursor obtained by flash column chromatography3e (0.598g, 1.86mmol),The yield is 93%.Purity is 99%,It is an oily substance.

Reference： [1]Patent: CN108997168,2018,A .Location in patent: Paragraph 0080; 0081; 0082

65
[ 647-42-7 ]
[ 1402556-57-3 ]
C₇₂H₃₀F₇₈O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1-chloro-3-hydroxy-1,1,3,3-tetrabutyldistannoxane; at 150℃; for 24h;Dean-Stark; Inert atmosphere;	To a trifluorotoluene solution (15 ml) of triphenylene-2,3,6,7,10,11-hexacarboxylic acid hexaethyl ester (200 mg, 0.30 mmol), <strong>[647-42-7]2-(perfluorohexyl)ethanol</strong> (1.06 g, 2 .91 mmol) and 1-chloro-3-hydroxy-1,1,3,3-tetrabutyldistannoxane (65.0 mg, 0.12 mmol) was added in order, then a Dean-Stark trap and a reflux condenser were used, The mixture was heated under reflux under Ar for 24 hours with stirring (temperature: 150 C.).The resulting reaction mixture was evaporated to dryness under reduced pressure.Recrystallization (dichloroethane) was performed on the residue, and Comparative Compound 1 (HC2TPFC6) was isolated in a yield of 92% (713 mg, 0.28 mmol).

Reference： [1]Patent: JP2018/199628,2018,A .Location in patent: Paragraph 0059

66
[ 17134-17-7 ]
[ 647-42-7 ]
C₃₅H₇₂O₁₉ [ No CAS ]
C₆₇H₁₀₂F₂₆O₃₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%		All glassware used for the synthesis was dried in an oven at 110 C overnight. (0191) To a 200 mL 2-neck flask equipped with a stir bar was added 12 g (0.016 mol) of XMer tetraol (MW = 771 Da), degassed overnight with gentle stirring at 60 C, and then purged with N2 (0192) To a 500 mL 2-neck oven-dried flask equipped with a stir bar was added 9 g (0.033 mol) triethylene glycol (TEG) bis chloroformate. The flask was degassed for 15 min and then purged with dry N2. (0193) After purging, 65 mL of anhydrous CHCI3 was transferred into the flask by means of a syringe. The TEG bis chloroformate was stirred to dissolve in the solvent. To a 50 mL addition funnel was added 15 g (0.033 mol) of Capstone 62-AL fluoroalcohol (1 H, 1 H,2H,2H-perfluoro-1-octanol), and degassed for 15 min and purged with dry N2. To this addition funnel was added 20 mL of anhydrous CHCI3 followed by 3 g of anhydrous pyridine, and the flask shaken to dissolve all reagents. The addition funnel was attached to the 500 mL reaction flask which was cooled in ice and dropwise addition of Capstone 62-AL fluoroalcohol to the TEG bis chloroformate was performed. The addition took 1 h to complete, and the reaction was allowed to proceed for additional 10 min at room temperature (25 C) under N2 atmosphere to form a partially fluorinated TEG bis chloroformate-Capstone 62-AL intermediate. While the partial fluorination was in progress, anhydrous CHCI3 (122 mL) was added to the flask containing the XMer tetraol via a cannula, followed by 2.5 g of anhydrous pyridine, and the mixture was stirred to dissolve the reagents. Next, the X-Mer tetraol solution was transferred to the 500 mL reaction vessel using a 20 gauge cannula in a slow continuous stream while the reaction vessel was cooled in an ice bath until all of the XMer diol solution had been added. The ice bath was removed and the reaction was allowed to proceed at room temperature for additional 10 min. The temperature was then raised to 50 C and the reaction was allowed to run overnight. All additions and transfers were conducted under a dry N2 atmosphere to avoid any contact with air. The purification involved rotary evaporation of CHCI3 from the reaction mixture, addition of THF, and separation of the pyridine salts by vacuum filtration. The product was treated with 1 N HCI and extracted in dichloromethane-water mixture to remove excess pyridine, then neutralized with 1 N NaOH solution. The bottom organic layer was collected, further washed twice with distilled water and then rotary evaporated. Finally, the product was dissolved in minimum isopropyl alcohol (IPA), precipitated out in hexanes, washed 2x with hexanes, and dried under vacuum. The product was dried overnight at 60 C in a vacuum oven to yield the product as a viscous liquid (59% yield). (0194) The purified product was characterized by GPC (molecular weight based on polystyrene standards), and elemental analysis for fluorine. The average molecular weight (polystyrene equivalent) was 2322 g/mol. Polydispersity = 1.12. Elemental analysis shows F = 25.8% Thermal decomposition temperature (TGA, under N2), at first onset: 221 C (at 10 wt% loss). The chemical structure of compound 3 (XMer-1226-PCT-PC) is shown in Figure 3.

Reference： [1]Patent: WO2019/169500,2019,A1 .Location in patent: Page/Page column 17-18

67
[ 17134-17-7 ]
[ 647-42-7 ]
C₄₅H₉₂O₂₂ [ No CAS ]
C₇₇H₁₂₂F₂₆O₃₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%		All glassware used for the synthesis was dried in an oven at 110 C overnight. (0185) To a 200 mL 2-neck oven-dried flask equipped with a stir bar was added 50 g (0.048 mol) YMer diol (MW = 1000 Da) and degassed overnight with gentle stirring at 60 C. Then, the YMer diol was purged with dry N2, 53 mL of anhydrous chloroform (CHCI3) were added to the flask using a cannula, followed by 15 g of anhydrous pyridine. The reaction mixture was stirred to dissolve the reagents and obtain a homogeneous solution. To a 1 L, 2-neck oven-dried flask equipped with a stir bar was added 60.9 g (0.221 mol) triethylene glycol (TEG) bis chloroformate. The flask was degassed for 15 min and then purged with dry N2. After purging, 157 mL of anhydrous CHCI3 were transferred into the flask by means of a cannula. The TEG bis chloroformate was stirred to dissolve in the solvent. To a 500 mL 2-neck flask was added 73.59 g (0.202 mol) of Capstone 62-AL fluoroalcohol (1 H, 1 H,2H,2H-perfluoro-1-octanol), then degassed for 15 min and purged with dry N2. (0186) To this was added 314 mL of anhydrous CHCI3 followed by 28 g of pyridine. The flask was stirred to dissolve all the reagents. The Capstone 62-AL fluoroalcohol solution was transferred to a 500 mL addition funnel that was previously degassed and purged with N2 using a cannula. The addition funnel was attached to the 1 L reaction vessel containing the TEG bis chloroformate solution that was cooled in an ice bath. The addition of the fluoroalcohol was done dropwise under N2 for 1 h. Stirring was kept to a minimum during the reaction to form a partially fluorinated TEG bis chloroformate- Capstone 62-AL fluoroalcohol intermediate. Next, the YMer diol solution was transferred to the 1 L reaction vessel using a 20 gauge cannula in a slow continuous stream while the reaction vessel was cooled under an ice bath until all of the YMer diol solution had been added. The ice bath was removed and the reaction was allowed to proceed at room temperature for additional 10 min. The temperature was then raised to 50 C and the reaction was allowed to run overnight. All additions and transfers were conducted under a dry N2 atmosphere to avoid any contact with air. (0187) The crude product was purified by first removing the CHCI3 solvent on a rotary evaporator, dissolving the crude product in minimum THF, and cooling with ice bath for 20 min to precipitate the pyridine salts. The solution was vacuum filtered and the THF was evaporated using a rotary evaporator. The product was treated with 1 N HCI and extracted in dichloromethane-water mixture to remove excess pyridine, then neutralized with 1 N NaOH solution. The bottom organic layer was collected, washed twice with distilled water, and then rotary evaporated. Finally, the product was dissolved in minimum isopropyl alcohol (IPA), precipitated out in hexanes, washed 2x with hexanes, and dried under vacuum. The product was dried overnight at 60 C in a vacuum oven to yield the product as a viscous liquid (59% yield). The purified product was characterized by GPC (molecular weight based on polystyrene standards), and elemental analysis for fluorine. The average molecular weight (polystyrene equivalent) was 3422 g/mol. Polydispersity = 1.15. Elemental analysis: F = (0188) 19%). Thermal decomposition temperature (TGA, under N2), at first onset: 203 C (at 5% wt loss). The chemical structure of compound 2 (YMer-1226-PCT-PC) is shown in Figure 2.

Reference： [1]Patent: WO2019/169500,2019,A1 .Location in patent: Page/Page column 16-17

68
[ 67-66-3 ]
[ 647-42-7 ]
[ 67-64-1 ]
[ 2144-53-8 ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 10913 - 10917

69
[ 75-25-2 ]
[ 647-42-7 ]
[ 67-64-1 ]
[ 2144-53-8 ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 10913 - 10917

70
[ 647-42-7 ]
[ 67362-78-1 ]
[ 1293408-06-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine; In ethyl acetate; at 20℃; for 24h;	The synthesis of the monomer, ABCF13, was accomplished in three stages: (I) preparation of p-acryloyloxybenzoic acid, ABA, (II) preparation of p-acryloyloxybenzoyl chloride, ABC and (III) preparation of ABCF13. The syntheses of both p-acryloyloxybenzoic acid (ABA) and p-acryloyloxybenzoyl chloride (ABC) were announced in our previous work [32,33]. The monomer was prepared by the condensation reaction between 3,3,4,4,5,5,6,6,7,7,8,8,8-dodecafluoro-1-octanol (DFO) and ABC. Typically, 4.75 mmol of DFO and 4.75 mmol of triethylamine was dissolved in 100 mL of EtOAc in a flask equipped with a magnetic stirrer. 4.75 mmol of ABC dissolved in 100 mL of EtOAc was added dropwise at room temperature by stirring the mixture simultaneously. After the reaction was completed, triethylamine hydrochloride salt formed during the reaction was extracted from the product by successive washings (3-4 times) with water. The product was then dissolved in EtOAc. The remaining water in the solution was removed by adding Na2SO4 as drying agent and then by filtering off. Finally, the solvent was evaporated and the product was purified by repeated recrystallizations from methanol, and dried in vacuum at the room temperature.The reaction yield was founded to be 81 %. FTIR, DSC, 1H NMR,High Resolution Mass Spectroscopy (HRMS) and elemental analysis techniques were used for the chemical characterization of the monomer synthesized. The plain reaction steps for the synthesis of ABCF13 was displayed in Fig. 1. White solid: 81 % yield. melting point; 44 C with respect to DSC. 1H-NMR (400 MHz, CDCl3, 25 C, TMS): delta2.60-4.62 (4H, -CH2), 6.06-6.32-6.60 (3H, -CH), 7.22-8.08 (4H,ArH). IR (KBr) (nu max, cm-1) 2976 (-CH3), 1739 and 1716 (-C = O),1635 and 1508 (C = C), 1284-1122 (-C-F and -C-O-C) and 908-765(C-H). Elemental analysis calcd. for C18H11F13O4; C, 40.17; H, 2.06.Found: C, 40.67; H, 2.14. HRMS: m/z (ESI-TOF, [M+H]+) calcd. forC18H12F13O4: 539.0528. Found: 539.0527.

Reference： [1]Journal of Fluorine Chemistry,2020,vol. 233

71
[ 647-42-7 ]
[ 701209-98-5 ]
C₂₅H₁₈F₂₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca. 75%		To a DMF solution, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-ol (2.13 g, 5.85 mmol, 2.0 equivalents) is added into the flask followed by adding 60% NaH (234 mg, 5.85 mmol, 2.0 equivalents) and then the mixture is stirred for 2 hrs; then 3,3-bis(bromomethyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine (1.0 g, 2.92 mmol, 1.0 equivalent) is added slowly into the mixture. After reacting for 18 hrs at 100 C., water is added into the flask. The resulting solution is extracted with dichloromethane. The organic phase is applied to silica gel flash column and washed with dichloromethane (DCM)/hexane to obtain a product of about 2 g. The yield is about 75%.

Reference： [1]Patent: US2020/102286,2020,A1 .Location in patent: Paragraph 0056-0057

72
[ 108-55-4 ]
[ 647-42-7 ]
1H,1H,2H,2H-perfluoro-1-octyl glutaric acid monoester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; In tetrahydrofuran; at 100℃; for 4h;	To a solution of 1 /7,1 /-/,2/-/,2/-/-perfluoro-1 -octanol (5.1 8 g, 14.23 mmol) in THF (6 mL), glutaric anhydride (1 .78 g, 15.65 mmol) and DMAP (0.35 g, 2.85 mmol) were added. The mixture was stirred at 100C for 4 hours. Thereafter, the mixture was cooled to 10C and 100 mL of water was added . The white precipitate was filtered off and washed with 10 mL cold water. The precipitate was dissolved in ethyl acetate and a saturated NaHC03 solution was added. The aqueous phase was separated and HCI was added to aqueous to pH~6. The aqueous layer was extracted three times with ethyl acetate. The organic fractions were combined, washed with brine, dried with MgS04 and concentrated to obtain 1 H, 1 /7,2/7,2/7-perfluoro- 1 -octyl glutaric acid monoester 2k (5.78g, yield = 85%) Spectral analysis: 1 H NMR (500 MHz, acetone-d6): delta = 4.43 (t, J = 6.2 Hz, 2H), 2.74 - 2.61 (m, 2H), 2.43 (t, J = 7.4 Hz, 2H), 2.38 (t, J = 7.3 Hz, 2H), 1 .95 - 1 .85 (m, 2H). 19F NMR (470 MHz, acetone-d6): delta = -80.75 - -83.66 (m, 3F), -1 14.02 - -1 14.22 (m, 2F), -122.35 - - 122.63 (m, 2F), -123.44 - -123.60 (m, 2F), -124.14 - -124.35 (m, 2F), -126.79 - -126.98 (m, 2F). 13C NMR (126 MHz, acetone-d6): delta = 173.25, 172.1 1 , 55.87, 32.58, 32.44, 30.02, 19.87. 13C dec 19F NMR (126 MHz, acetone-d6): delta = 1 18.13, 1 17.15, 1 1 1 .10, 1 10.89, 1 10.28, 108.49.

Reference： [1]Patent: WO2020/84599,2020,A2 .Location in patent: Page/Page column 16; 24

73
[ 764-99-8 ]
[ 647-42-7 ]
1,1,2,2 tetrahydroperfluoro octanylvinyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.2%	With 1,10-Phenanthroline; palladium diacetate at 45℃; for 96h;	1-6 Example 3 45.0 g (284 mmol) of diethylene glycol divinyl ether, 516 g (1.35 mol) of 2- (perfluorohexyl) ethanol, 637 mg (2.84 mmol) of palladium acetate, 1,10-phenanthroline monohydrate in a 500 ml four-necked flask.By adding 511 mg (2.578 mmol) of the product and stirring at 45 ° C. for 96 hours,2- (Perfluorohexyl) ethyl vinyl ether was produced. Analysis using gas chromatography revealed that diethylene glycol divinyl ether was used as a reference.The yield was 98.2%.

Reference： [1]Current Patent Assignee: NOK CORPORATION - JP2021/63012, 2021, A Location in patent: Paragraph 0025-0027; 0029-0031

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Technical Information

• Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Alcohols are Weakly Basic • Alcohols as Acids • Alcohols Convert Acyl Chlorides into Esters • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alcoholysis of Anhydrides • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldol Addition • Alkene Hydration • Alkene Hydration • Alkyl Halide Occurrence • An Alkane are Prepared from an Haloalkane • Appel Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Carboxylic Acids React with Alcohols to Form Esters • Chloroalkane Synthesis with SOCI2 • Chromium Reagents for Alcohol Oxidation • Chugaev Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Convert Esters into Aldehydes Using a Milder Reducing Agent • Convert Haloalkanes into Alcohols by SN2 • Corey-Kim Oxidation • Decarboxylation of 3-Ketoacids Yields Ketones • Decomposition of Lithium Aluminum Hydride by Protic Solvents • Dess-Martin Oxidation • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylations Using Alcohols • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • Grignard Reagents Transform Esters into Alcohols • Grignard Reagents Transform Esters into Alcohols • Haloalcohol Formation from an Alkene Through Electrophilic Addition • Halogen and Alcohols Add to Alkenes by Electrophilic Attack • Halogen and Alcohols Add to Alkenes by Electrophilic Attack • Heat of Combustion • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydroboration-Oxidation • Hydroboration-Oxidation • Hydrolysis of Haloalkanes • Jones Oxidation • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Osmium Tetroxide Reacts with Alkenes to Give Vicinal Diols • Osmium TetroxideReacts with Alkenes to Give Vicinal Diols • Oxidation of Alcohols by DMSO • Oxymercuration-Demercuration • Preparation of Alcohols • Preparation of Alkenes by Dehydration of Alcohols • Preparation of Alkenes by Dehydration of Alcohols • Preparation of Alkoxides with Alkyllithium • Preparation of Amines • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Alcohols • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Ring Opening of an Oxacyclopropane by Lithium Aluminum Hydride • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation • Synthesis of Alcohols from Tertiary Ethers • Synthesis of an Alkyl Sulfonate • The Nucleophilic Opening of Oxacyclopropanes • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Transesterification • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vicinal Anti Dihydroxylation of Alkenes • Williamson Ether Syntheses

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[ CAS No. 647-42-7 ] {[proInfo.proName]}

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[ 647-42-7 ] Synthesis Path-Upstream 1~5

[ 647-42-7 ] Synthesis Path-Downstream 1~73

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Fluorinated Building Blocks

Aliphatic Chain Hydrocarbons

Alcohols

Trifluoromethyls

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