[ CAS No. 1481-27-2 ] {[proInfo.proName]}

Name: 1481-27-2|4-Fluoro-2-hydroxyacetophenone|98%
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Quality Control of [ 1481-27-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1481-27-2 ]

Product Details of [ 1481-27-2 ]

CAS No. :	1481-27-2	MDL No. :	MFCD00143203
Formula :	C₈H₇FO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HLTBTUXAMVOKIH-UHFFFAOYSA-N
M.W :	154.14	Pubchem ID :	2737326
Synonyms :

Calculated chemistry of [ 1481-27-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	38.62
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.54
Log Po/w (XLOGP3) :	2.11
Log Po/w (WLOGP) :	2.15
Log Po/w (MLOGP) :	1.55
Log Po/w (SILICOS-IT) :	2.09
Consensus Log Po/w :	1.89

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.46
Solubility :	0.531 mg/ml ; 0.00345 mol/l
Class :	Soluble
Log S (Ali) :	-2.52
Solubility :	0.461 mg/ml ; 0.00299 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.42
Solubility :	0.583 mg/ml ; 0.00378 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.16

Safety of [ 1481-27-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1481-27-2 ]

* 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 [ 1481-27-2 ]
Downstream synthetic route of [ 1481-27-2 ]

[ 1481-27-2 ] Synthesis Path-Upstream 1~4

1
[ 1481-27-2 ]
[ 74-88-4 ]
[ 51788-80-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate In acetonitrile at 20 - 75℃;	Preparation 31 -(4-FLUORO-2-METHOXYPHENYL)ETHANONE1 -(4-fluoro-2-hydroxyphenyl)ethanone (12.0 g, 77.9 mmol), iodomethane (6.38 ml, 101 mmol), potassiumcarbonate (14.0 g, 101 mmol) were heated at 75°C in ACN (200 ml) for 8h. The reaction mixture was brought to ambient temperature, filtered and then evaporated under reduced pressure to dryness. New ACN (150 ml), iodomethane (2 ml, 32 mmol) and potassiumcarbonate (4 g, 29 mmol) was added. The reaction mixture was heated at 75°C for 3 h. The reaction mixture was concentrated, EtOAc (100 ml) was added and the mixture was filtered and evaporated to give the title product (13.5 g, 100percent). MS m/z (rel. intensity, 70 eV) 168 (M+, 11 ), 153 (bp), 110 (23), 95 (21 ), 82 (12).

Reference： [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 15, p. 3823 - 3842
[2] Patent: WO2009/133110, 2009, A1, . Location in patent: Page/Page column 38
[3] Journal of Medicinal Chemistry, 1988, vol. 31, # 8, p. 1590 - 1595
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 4, p. 1583 - 1598
[5] Journal of Medicinal Chemistry, 1999, vol. 42, # 20, p. 4150 - 4160
[6] Patent: US4578387, 1986, A,

2
[ 1481-27-2 ]
[ 77-78-1 ]
[ 51788-80-8 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1974, p. 119 - 125

3
[ 1481-27-2 ]
[ 95-92-1 ]
[ 128942-39-2 ]

Reference： [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6569 - 6584

4
[ 364-83-0 ]
[ 1481-27-2 ]
[ 98619-07-9 ]

Reference： [1] Organic Preparations and Procedures International, 2009, vol. 41, # 5, p. 419 - 421

[ 1481-27-2 ] Synthesis Path-Downstream 1~50

1
[ 701-83-7 ]
[ 1481-27-2 ]

Yield	Reaction Conditions	Operation in experiment
86%		Take <strong>[701-83-7]3-fluorophenyl acetate</strong> (11 g, 71.4 mmol) into a two-necked flask,Anhydrous aluminum trichloride (19 g, 142.8 mmol) was added in portions under an ice bath,It was then heated to 190 C and stirred for one hour.After completion, cool to room temperature.Add a mixed solvent of ice water, hydrochloric acid and dichloromethane to the solid,The resulting mixture was stirred for 15 minutes and the phases were separated.The organic phase was washed successively with water and a saturated sodium chloride solution,Dry over anhydrous sodium sulfate and concentrate under reduced pressure.The target product was obtained as a yellow oily liquid (9.46 g, yield: 86%).
67.5%	With aluminum (III) chloride; at 180℃; for 3h;Inert atmosphere;	R3 - A mixture of R2 (190 g, 1.23 mol) and AlCb (295 g, 2.22mol) was stirred at 180 C for 3 h under N2 atmosphere. The mixture was cooled to room temperature and was added cold water (1 L), extracted with DCM (1000 mL x 2). The combined organic layer was washed with brine (1000 mL), dried over Na2SO4 and evaporated in vacuum to give the crude product which was purified by column chromatography on silica gel to give R3 (104 g, yield 67.5%) as a white solid. 1H NMR (CDCl3, 400 MHz): d (ppm) 2.62 (s, 3H), 6.63-6.69 (m, 2H), 7.73-7.79 (m, 1H), 12.60 (s, 1H).
	With hydrogenchloride;aluminium trichloride; In dichloromethane;	EXAMPLE 16 Preparation of 4'-Fluoro-2'-hydroxyacetophenone m-Fluorophenyl acetate (123 g, 0.798 mol) is cooled with an ice-bath, treated portionwise with aluminum chloride (150 g, 1.12 mol), stirred at 190 C. for one hour, and cooled to obtain a solid. A mixture of ice, water and hydrochloric acid, and methylene chloride are added to the solid. The resultant mixture is stirred for several minutes, and the phases are separated. The organic phase is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title product (99.0 g) which is identified by 1H NMR spectral analysis.

	With hydrogenchloride;aluminium trichloride; In dichloromethane;	EXAMPLE 14 Preparation of 4'-Fluoro-2'-hydroxyacetophenone STR142 m-Fluorophenyl acetate (123 g, 0.798 mol) is cooled with an ice-bath, treated portionwise with aluminum chloride (150 g, 1.12 mol), stirred at 190 C. for one hour, and cooled to obtain a solid. A mixture of ice, water and hydrochloric acid, and methylene chloride are added to the solid. The resultant mixture is stirred for several minutes, and the phases are separated. The organic phase is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title product (99.0 g) which is identified by 1 H NMR spectral analysis.
	aluminium trichloride;	EXAMPLE 23 Preparation of 4'-Fluoro-2'-hydroxyacetophenone m-Fluorophenyl acetate (123 g, 0.798 mol) is cooled with an ice-bath, treated portionwise with aluminum chloride (150 g, 1.12 mol), stirred at 190 C for one hour, and cooled to obtain a solid. A mixture of ice, water and hydrochloric acid, and methylene chloride are added to the solid.
	With hydrogenchloride;aluminium trichloride; In dichloromethane;	EXAMPLE 11 Preparation of 4'-Fluoro-2'-hydroxyacetophenone m-Fluorophenyl acetate (123 g, 0.798 mol) is cooled with an ice-bath, treated portionwise with aluminum chloride (150 g, 1.12 mol), stirred at 190 C. for one hour, and cooled to obtain a solid. A mixture of ice, water and hydrochloric acid, and methylene chloride are added to the solid. The resultant mixture is stirred for several minutes, and the phases are separated. The organic phase is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title product (99.0 g) which is identified by 1H NMR spectral analysis.
	With aluminum (III) chloride; at 190℃; for 1h;Cooling with ice-bath;	REFERENCE EXAMPLE 13 Preparation of 4'-Fluoro-2'-hydroxyacetophenone m-Fluorophenyl acetate (123 g, 0.798 mol) is cooled with an ice-bath, treated portionwise with aluminum chloride (150 g, 1.12 mol), stirred at 190 C for one hour, and cooled to obtain a solid.. A mixture of ice, water and hydrochloric acid, and methylene chloride are added to the solid.. The resultant mixture is stirred for several minutes, and the phases are separated.. The organic phase is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title product (99.0 g) which is identified by 1H NMR spectral analysis.
	With aluminum (III) chloride; at 160℃; for 1.5h;	To 122 g (0.79 mol) of <strong>[701-83-7]3-fluorophenylacetate</strong> was added Aids (137 g, 1.03 mol) and theresulting mixture was heated at 160 C for 1.5 h then cooled at 0 C. HC1 IN was carefully addedfollowed by Et2O. The aqueous phase was extracted(2X) with Et2O and the combined organic phasewashed with brine, dried over Na2SO4 and evaporated to give the title compound.
7.5 g	With aluminum (III) chloride; at 190℃; for 1h;	4-fluorophenyl acetate (10.5 g, 68.1 mmol) was added and aluminum chloride (12.7 g, 95.3 mmol) was added in portions on an ice bath. 1.4-2eq), stirred at 190C for one hour, cooled to give a solid. A mixture of ice, water, hydrochloric acid and dichloromethane was added to the solid. The resulting mixture was stirred for several minutes and the phases were separated. The organic phase was washed sequentially with water, saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the desired product (7.5 g) as a yellow oil.

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 814 - 820
[2]Patent: CN110229173,2019,A .Location in patent: Paragraph 0033; 0037-0039
[3]Journal of Medicinal Chemistry,1988,vol. 31,p. 1590 - 1595
[4]Journal of Medicinal Chemistry,2018,vol. 61,p. 3037 - 3058
[5]Patent: WO2020/33604,2020,A1 .Location in patent: Page/Page column 30
[6]Journal of Chemical Research, Miniprint,1998,p. 2678 - 2695
[7]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 323 - 329
[8]Journal of Medicinal Chemistry,1999,vol. 42,p. 4150 - 4160
[9]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 5996 - 6001
[10]Patent: US6355796,2002,B1
[11]Patent: US6140270,2000,A
[12]Patent: EP908457,1999,A1
[13]Patent: US6191275,2001,B1
[14]Patent: EP1150962,2004,B1 .Location in patent: Page 34
[15]Patent: WO2004/108720,2004,A1 .Location in patent: Page 61
[16]Journal of Medicinal Chemistry,2014,vol. 57,p. 6458 - 6467
[17]Patent: CN105085427,2018,B .Location in patent: Paragraph 0331; 0333; 0337; 0338

2
[ 1481-27-2 ]
[ 4637-24-5 ]
[ 138469-95-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	at 95℃; for 4h;	General procedure: The appropriate 2?-hydroxyacetophenones (1 equiv) were diluted using dimethylformamide-dimethylacetal (1.5 equiv.) and the resulting mixture stirred at 95C for 4h. The volatiles were evaporated in vacuo to yield the enaminone intermediates 1A to 8A. (E)-3-(dimethylamino)-1-(4-fluoro-2-hydroxyphenyl)prop-2-en-1-one (3A) Yellow solid (147mg, 73%) m.p. 116-118C Rf (EtOAc: Hexane 4:6) 0.4 1H NMR (400 MHz, CDCl3) delta 7.85 (d, J = 12.1 Hz, 1H, H-3), 7.66 (dd, J = 8.9, 6.6 Hz, 1H, H-6?), 6.58 (dd, J = 10.6, 2.6 Hz, 1H, H-3?), 6.54 - 6.45 (m, 1H, H-5?), 5.65 (d, J = 12.1 Hz, 1H, H-2), 3.17 (d, J = 2.9 Hz, 3H, N-CH3), 2.94 (d, J = 5.1 Hz, 3H, N-CH3). 13C NMR (101 MHz, CDCl3) delta 190.5, 167.4, 165.4, 154.8, 130.2 (d, 3JCF = 11.3 Hz, C-6?), 117.1, 105.8 (d, 2JCF = 22.4 Hz, C-5?/C-3?), 104.6 (d, 2JCF = 23.0 Hz, C-3?/C-5?), 89.8, 45.4, 37.4
	at 120℃; for 2h;	Example 39A 7-fluoro-4H-chromen-4-one A mixture of l-(4-fluoro-2-hydroxyphenyl)ethanone (1. g, 6.49 mmol) and 1,1- dimethoxy-N,N-dimethylmethanamine (0.948 mL, 7.14 mmol) was heated at 120 C for 2 hours, and cooled down . The precipitated orange solid was filtered, washed with heptane, and dried to yield (E)-3-(dimethylamino)-l-(4-fluoro-2-hydroxyphenyl)prop-2-en-l-one which was dissolved in dichloromethane (120 mL) and treated with concentrated HC1 (15 mL). The mixture was refluxed for 2 hours. Water layer was removed and organic layer was washed with brine (50 mL x 2). The organics was concentrated and the residue was purified by chromatography on 80 g silica gel cartridge, eluting with 5-30 % ethyl acetate in heptane to provide the title compound (760 mg, 71.4 % yield) as white solid. 1H NMR (400 MHz, CDC13) delta 8.23 (dd, J= 9.6, 6.2 Hz, 1H), 7.83 (d, J= 6.0 Hz, 1H), 7.19 - 7.08 (m, 2H), 6.33 (d, J= 6.1 Hz, 1H); MS (ESI+) m/z 165 (M+H)+ .

Reference： [1]Archiv der Pharmazie,1991,vol. 324,p. 949 - 951
[2]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2510 - 2513
[3]Journal of Medicinal Chemistry,2006,vol. 49,p. 3973 - 3981
[4]Organic Letters,2009,vol. 11,p. 4010 - 4013
[5]Patent: WO2016/69757,2016,A1 .Location in patent: Page/Page column 166
[6]Organic Letters,2017,vol. 19,p. 146 - 149
[7]Journal of Medicinal Chemistry,2018,vol. 61,p. 1436 - 1449

3
[ 1481-27-2 ]
[ 4637-24-5 ]
[ 138469-95-1 ]

Yield	Reaction Conditions	Operation in experiment
	In para-xylene; for 12h;Reflux;	General procedure: Dimethylformamide dimethylacetal (DMFDMA) (1.19 g, 10 mmol) and 1-(2-hydroxyphenyl) ethanone (1.36 g, 10 mmol) were dissolved in p-xylene (2 mL). And the mixture was refluxed for 12 h, then a yellow precipitate formation. The precipitate was filtered out and washed with petroleum ether for three times. The solid was dried under vacuum, and 1.79 g (94% yield) L5 was obtained.
	at 100℃; for 2h;	General procedure: A mixture of o-hydroxyacetophenone 1a (136 mg, 1 mmol, 1 equiv.) and dimethylformamide dimethylacetal (120 mg, 1 mmol, 1 equiv.) was heated for 2 hours at 100C. After cooling to 25C, a pre-prepared solution of malononitrile (66 mg, 1 mmol, 1 equiv.) and SeO2 (332 mg, 3 mmol, 3equiv.) in DMSO (1 mL), stirred at 25 C for 20 min, was added at 25 C. The reaction mixture was stirred for a further 30 min, then water was added (3 mL). The resulting precipitate was filtered off, washed with water (3 x 10 mL) and dried under a fume hood overnight at 25C to give pure product 3a.

Reference： [1]Archiv der Pharmazie,1994,vol. 327,p. 267 - 269
[2]Tetrahedron,2012,vol. 68,p. 5046 - 5052
[3]Chemical Communications,2016,vol. 52,p. 12306 - 12309
[4]Synlett,2018,vol. 29,p. 1215 - 1218
[5]Chinese Chemical Letters,2018,vol. 29,p. 963 - 966
[6]RSC Advances,2018,vol. 8,p. 26828 - 26836

4
[ 1481-27-2 ]
[ 74-88-4 ]
[ 51788-80-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In acetonitrile; at 20 - 75℃;	Preparation 31 -(4-FLUORO-2-METHOXYPHENYL)ETHANONE1 -(4-fluoro-2-hydroxyphenyl)ethanone (12.0 g, 77.9 mmol), iodomethane (6.38 ml, 101 mmol), potassiumcarbonate (14.0 g, 101 mmol) were heated at 75C in ACN (200 ml) for 8h. The reaction mixture was brought to ambient temperature, filtered and then evaporated under reduced pressure to dryness. New ACN (150 ml), iodomethane (2 ml, 32 mmol) and potassiumcarbonate (4 g, 29 mmol) was added. The reaction mixture was heated at 75C for 3 h. The reaction mixture was concentrated, EtOAc (100 ml) was added and the mixture was filtered and evaporated to give the title product (13.5 g, 100%). MS m/z (rel. intensity, 70 eV) 168 (M+, 11 ), 153 (bp), 110 (23), 95 (21 ), 82 (12).
	With hydrogenchloride; In N-methyl-acetamide;	C. Preparation of 2-methoxy-4-fluoroacetophenone To a solution of 13.9 g. of 2-hydroxy-4-fluoroacetophenone in 75 ml. of dry dimethylformamide were added 30 ml. of methyl iodide. The solution was cooled to 0 C. and 4.1 g. of a 50% oil dispersion of sodium hydride were carefully added. After stirring for one hour at 0 C., the reaction was extracted with ethyl acetate. The organic extract was washed three times with 200 ml. each of 1N hydrochloric acid. The ethyl acetate solution was then dried and removed in vacuo. This reaction and a subsequent identical reaction provided a total of 28 g. of 2-methoxy-4-fluoroacetophenone as an oil which was used in the subsequent step without further purification.

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842
[2]Patent: WO2009/133110,2009,A1 .Location in patent: Page/Page column 38
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 3068 - 3087
[4]Journal of Medicinal Chemistry,1988,vol. 31,p. 1590 - 1595
[5]Journal of Medicinal Chemistry,2014,vol. 57,p. 1583 - 1598
[6]Journal of Medicinal Chemistry,1999,vol. 42,p. 4150 - 4160
[7]Patent: US4578387,1986,A

5
[ 1481-27-2 ]
[ 77-78-1 ]
[ 51788-80-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1974,p. 119 - 125

6
[ 1481-27-2 ]
[ 67-64-1 ]
[ 111477-98-6 ]

Yield	Reaction Conditions	Operation in experiment
70.7%	With pyrrolidine; In benzene; at 80℃; for 3h;	To l-(4-fluoro-2-hydroxyphenyl)ethanone (5.75 g, 37.3 mmol) and propan-2-one (12 mL, 37.3 mmol) in benzene (50 mL) was added pyrrolidine (3.11 mL, 37.3 mmol) and the reaction heated at 80 0C for 3 hours. The reaction was diluted with ethyl acetate (50 mL), washed with IN HCl (50 mL), brine (50 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography, eluting with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate, to provide the title compound (5.12 g, 70.7% yield).
53%	With pyrrolidine; In benzene; for 1h;Heating / reflux;	Step 1 7-Fluoro-2,2-dimethyl-chroman-4-one l-(4-Fluoro-2-hydroxy-phenyl)-ethanone (5.0 g, 32.44 mmol), acetone (11.92 mL,162.2 mmol) and pyrrolidine (2.7 mL, 32.44 mmol) were dissolved in 20 mL benzene, and the reaction mixture was refluxed for four hours. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and 1 N HCl. The organic layer was dried over MgSC>4, and solvent was evaporated under reduced pressure. The resulting residue was chromatographed (15% ethyl acetate in hexanes eluting through silica) and solvent was removed to yield 3.33 g (17.16 mg, 53%) of 7-nuoro-2,2-dimethyl- chroman-4-one as an oil. MS: 195 (M+H)+.
53%	With pyrrolidine; In benzene; for 4h;Heating / reflux;	l-(4-Fluoro-2-hydroxy-phenyl)-ethanone (5.0 g, 32.44 mmol), acetone (11.92 mL, 162.2 mmol) and pyrrolidine (2.7 mL, 32.44 mmol) were dissolved in 20 mL benzene, and the reaction mixture was refluxed for four hours. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and 1 N HCl. The organic layer was dried over MgSO4, and solvent was evaporated under reduced pressure. The resulting residue was chromatographed (15% ethyl acetate in hexanes eluting through silica) and solvent was removed to yield 3.33 g (17.16 mg, 53%) of 7-fluoro-2,2-dimethyl- chroman-4-one as an oil. MS: 195 (M+H)+.

With pyrrolidine; at 20℃; for 5h;Heating / reflux;

EXAMPLE 65 1-(7-fluoro-2,2-dimethylchroman-4-yl)-3-(1-(2-methoxyethyl)-1H-indazol-4-yl)urea EXAMPLE 65A 7-fluoro-2,2-dimethylchroman-4-one; A mixture of 4-fluoro-2-hydroxyacetophenone (Aldrich, 1.54 g, 10 mmol), acetone (0.95 mL, 12.9 mmol), and pyrrolidine (0.83 mL, 9.94 mmol) was stirred in 3 mL toluene at room temperature for 1 h and at reflux (Dean-Stark trap) for 4 hours. After cooling to room temperature, the mixture was diluted with ether (30 mL) and was washed with 2N HCl (10 mL) and H2O (10 mL). Drying over Na2SO4 and evaporation of volatiles in vacuo afforded the crude title compound, which was used without further purification.

Reference： [1]Patent: WO2009/158426,2009,A1 .Location in patent: Page/Page column 73
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 8760 - 8764
[3]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1393 - 1396
[4]Patent: WO2006/66746,2006,A1 .Location in patent: Page/Page column 32
[5]Patent: WO2006/66756,2006,A1 .Location in patent: Page/Page column 26
[6]Patent: US2007/99954,2007,A1 .Location in patent: Page/Page column 31
[7]Journal of Medicinal Chemistry,2010,vol. 53,p. 7405 - 7413

7
[ 1481-27-2 ]
[ 79099-07-3 ]
[ 936648-33-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	With pyrrolidine; In methanol; at 60℃; for 2h;	<strong>[1481-27-2]4-Fluoro-2-hydroxyacetophenone</strong> (0.33 g, 2.14 mmol) was dissolved in methanol (5 mL) and pyrrolidine (0.21 mL, 2.57 mmol) and N-Boc-4-piperidone (0.51 g) were added. 2.57 mmol), the reaction solution was stirred at 60C for 2 hours, the solvent was concentrated in the reaction solution, dissolved in ethyl acetate (50 mL), and washed with 1N hydrochloric acid (100 mL) and saturated aqueous sodium chloride, respectively. After drying over anhydrous sodium sulfate, concentration, and the residue was subjected to silica gel column chromatography (petroleum ether/ethyl acetate=5:1) to give Compound 45-e (0.41 g, 57%).
33%	With pyrrolidine; In methanol; for 24h;	7-Fluorospirorchromene-2,4'-piperidin1-4(3H)-one Hydrochloride Hydrate A solution of 1-(4-fluoro-2-hydroxyphenyl)ethanone (200 g, 1.3 mol), tert-butyl 4-oxopiperidine-1- carboxylate (258 g, 1.3 mol) and pyrrolidine (108 mL, 1.3 mol) in methanol (800 mL) was stirred for 24 hours and then evaporated. Next the residue was dissolved in ethyl acetate, washed with water, 0.5 N HCI,"NaH^O"3~s^[ntioTi^nd~s^tu7ate3 aqueous NaCI and passed" through" a thinTayeff Sitheta2 and Na2SO4. The filtrate was evaporated, and the residue was washed with hexane/ethyl acetate (9:1) mixture and subjected to chromatography (hexane/ethylacetate 90:10-» 80:20) to afford N-Boc-7- Fluorospiro[chromene-2,4'-piperidin]-4(3H)-one in 33% (144 g) yield, 236 (M-Boc; ES+).HCI (90 mL) was added to a solution of N-Boc-7-Fluorospiro[chromene-2,4'-piperidin]-4(3H)-one] (44.2 g, 0.132 mol) in isopropanol (150 mL), and the obtained mixture was refluxed for 3 hours. After this, the mixture was evaporated, and the residue was co-evaporated twice with isopropanol, washed with ether and dried to give 7-fluorospiro[chromene-2,4'-piperidin]-4(3H)-one hydrochloride hydrate in 99% (35.8 g) yield, 236 (API+).

Reference： [1]Patent: CN103304571,2018,B .Location in patent: Paragraph 0432-0434
[2]Patent: WO2008/65508,2008,A1 .Location in patent: Page/Page column 21
[3]Journal of Medicinal Chemistry,2002,vol. 45,p. 492 - 503
[4]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 746 - 754

8
[ 1481-27-2 ]
[ 95-92-1 ]
[ 128942-39-2 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6569 - 6584

9
[ 1481-27-2 ]
[ 450-93-1 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842

10
[ 1481-27-2 ]
[ 221559-20-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydroxylamine hydrochloride; sodium acetate; In methanol; at 70℃; for 4h;	1- (4-Fluoro-2-hydroxyphenyl) ethanone (6.3 g, 41 mmol) , hydroxylamine hydrochloride (5.70 g, 82 mmol) and anhydrous sodium acetate (7.73 g, 94 mmol) were dissolved in anhydrous methanol (60 mL) . The mixture was refluxed for 4 h by heating at 70 in an oil-bath, then the reaction was stopped. The mixture was cooled to 25 , and to the mixture was added water (200 mL) . The resulting mixture was stirred for 0.5 h, and then filtered. The filter cake was washed with water (300 mL) for three times to give a gray solid (6.60 g) , yield: 95%.
91%	With hydroxylamine hydrochloride; sodium acetate; In methanol; for 2h;Heating / reflux;	EXAMPLE 1 Step 1: A mixture of 4-fluoro-2-hydroxyacetophenone 1 (50 g, 324 mmol), hydroxylamine hydrochloride (45 g, 648 mmol), and sodium acetate (40 g, 488 mmol) in anhydrous MeOH (1 L) was refluxed for 2 h. After cooling to RT, the reaction mixture was slowly poured onto ice and stirred for 30 min. The white precipitate thus obtained was filtered through suction and then dissolved in CH2Cl2, dried (MgSO4), filtered, and concentrated to give 2 as a white solid (50 g, 91% yield) which was used without further purification for the next step.
88%	With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; at 78℃; for 1.5h;	4-fluoro-2-hydroxyacetophenone (7 g, 45.4 mmol),Hydroxylamine hydrochloride (5.05g, 72.7mmol) and sodium acetate trihydrate (10g, 72.7mmol)The mixture was added to 60 mL of EtOH-H2O (3: 1) mixed solvent.The mixture was heated at 78 C under reflux for 90 minutes.The reaction system was cooled, and the solution was concentrated under reduced pressure until a solid precipitated.Water was added again, and the precipitated solid was filtered by suction.The filter cake was washed with water,Drying gave the target compound as a white solid (6.79 g, yield: 88%).

With hydroxylamine hydrochloride; sodium acetate; In methanol; for 1h;Heating / reflux;

REFERENCE EXAMPLE 14Preparation of 4'-Fluoro-2'-hydroxyacetophenone, oxime [45.1] A mixture of 4'-fluoro-2'-hydroxyacetophenone (99.0 g, 0.640 mol), hydroxylamine hydrochloride (89.0 g, 1.28 mol), and sodium acetate (79.0 g, 0.960 mol) in methanol is refluxed for one hour and poured into an ice-water mixture. The resultant aqueous mixture is filtered to obtain a solid. The solid is dissolved in methylene chloride, and the resultant organic solution is dried over anhydrous magnesium sulfate, concentrated in vacuo, diluted with hexanes, and filtered to give the title product as a solid (55.0 g, mp 112-114 C) which is identified by 1H NMR spectral analysis.

Reference： [1]Patent: WO2019/62802,2019,A1 .Location in patent: Paragraph 00209
[2]Patent: US2007/72867,2007,A1 .Location in patent: Page/Page column 4-5
[3]Patent: CN110229173,2019,A .Location in patent: Paragraph 0033; 0040-0042
[4]Journal of Medicinal Chemistry,2018,vol. 61,p. 3037 - 3058
[5]Patent: EP1150962,2004,B1 .Location in patent: Page 34

11
[ 1481-27-2 ]
[ 100-44-7 ]
[ 67-64-1 ]
[ 106245-03-8 ]

Yield	Reaction Conditions	Operation in experiment
11 parts (58%)	With potassium iodide; potassium carbonate	16 Example 16 Example 16 A mixture of 13 parts of 1-(4-fluoro-2-hydroxyphenyl)ethanone, 14.9 parts of (chloromethyl)benzene, 16.4 parts of potassium carbonate, 0.1 parts of potassium iodide and 120 parts of 2-propanone was stirred overnight at reflux temperature. The reaction mixture was evaporated. The reaction mixture was poured into water. The product was extracted three times with trichloromethane. The combined extracts were dried, filtered and evaporated. The residue was crystallized from a mixture of 2-propanol and water. The product was filtered off and dried, yielding 11 parts (58%) of 1-[4-fluoro-2-(phenylmethoxy)phenyl]ethanone (intermediate 76).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US4689330, 1987, A

12
[ 1481-27-2 ]
[ 105-36-2 ]
[ 926648-01-3 ]

Yield	Reaction Conditions	Operation in experiment
90%		Step 1 :To a solution of 4-fluoro-2-hydroxyacetophenone (1.0 g, 6.5 mmol) and ethyl bromoacetate (0.80 mL, 7.2 mmol) in DMF (10.0 ml_), was added potassium carbonate (2.7 g, 19.5 mmol). The mixture was heated to 60C for 2h, then cooled to RT, diluted with EtOAc (40 mL) and quenched with H2O (15 mL). The two layers were separated, and the organic layer was washed twice with water, once with brine, dried over MgSO4, filtered and concentrated. The compound was purified by flash column chromatography on silica gel using a solvent gradient of EtOAc in hexane (from 0% to 20%) to provide compound 1a (1.4 g, 90% yield).

Reference： [1]Patent: WO2007/19674,2007,A1 .Location in patent: Page/Page column 41

13
[ 1481-27-2 ]
[ 106-95-6 ]
[ 956530-85-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 24h;	Step F 1. 1 -(2-(Allyloxy)-4-fluorophenyl)ethanoneA mixture of l-(4-fluoro-2-hydroxyphenyl)ethanone (7.50 g, 48.7 mmol), 3-bromoprop- 1-ene (6.48 g, 53.5 mmol), and potassium carbonate (13.5 g, 97.0 mmol) in DMF (75 mL) was vigorously stirred at rt for 24 h. The reaction mixture was diluted with water (100 mL) while stirring. The white precipitate was collected by vacuum filtration. The solid was rinsed with water (300 mL). The solid was dried under high vacuum to afford l-(2- (allyloxy)-4-fluorophenyl)ethanone (7.92 g, 40.0 mmol, 82 % yield) as a white solid. LCMS (M+Na)+ = 217.1. 'H NMR (500 MHz, chloroform-if) delta 7.82 (dd, J=8.7, 7.0 Hz, 1H), 6.71 (ddd, J=8.7, 7.6, 2.3 Hz, 1H), 6.66 (dd, J=10.8, 2.3 Hz, 1H), 6.08 (ddt, J=17.3, 10.6, 5.3 Hz, 1H), 5.55 - 5.41 (m, 1H), 5.41 - 5.29 (m, 1H), 4.63 (dt, J=5.4, 1.4 Hz, 2H), 2.62 (s, 3H).

Reference： [1]Patent: WO2012/162330,2012,A1 .Location in patent: Page/Page column 36-37
[2]Organic Letters,2018,vol. 20,p. 1363 - 1366

14
[ 654655-68-2 ]
[ 1481-27-2 ]
1-[2-(3-benzyl-6-bromo-quinolin-2-yloxy)-5-fluoro-phenyl]-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51.5%	With potassium carbonate; In dimethyl sulfoxide; at 130℃; for 12h;	Preparation ofl-[2-(3-Benzyl-6-bromo-quinolin-2-yloxy)-5-fluoro-phenyl]-ethanone; A mixture of l-(2-Hydroxy-phenyl)-ethanone] (023 g, 1 51 mmol) and potassium carbonate (0 23 g, 1 70 mmol) m anhydrous dimethylsulfoxide (6 mL) was heated to 130 0C for 12 h under inert atmosphere The mixture was poured into ice-water mixture, extracted with ethylacetate, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (silica gel 100-200 mesh, elutmg with 8% ethyl acetate in n-hexane) gave pure l-[2-(3- Benzyl-6-bromo-qumolm-2-yloxy)-5-fluoro-phenyl]-ethanone (0.28 g, 51 5%) as a pale yellow solid, Mp 115-117 0C. 1H NMR (400 MHz, CDCl3): delta 2.23 (s, 3 H), 4.22 (s, 2 H), 6 98 (dd, J = 9.2, 4.4 Hz, 1 H), 7.18-7 23 (m, 1 H), 726-7.37 (m, 5 H), 7 48 (d, /= 8 8 Hz, 1 H), 7.52 (dd, J= 8 8, 3 2 Hz, 1 H), 7.59 (dd, J= 8.8, 2.0 Hz, I H), 7.75 (s, 1 H), 7.84 (J = 2 0 Hz, 1 H). [M+H]+ = 450, 452.

Reference： [1]Patent: WO2009/91324,2009,A1 .Location in patent: Page/Page column 21

15
[ 364-83-0 ]
[ 1481-27-2 ]
[ 98619-07-9 ]

Reference： [1]Organic Preparations and Procedures International,2009,vol. 41,p. 419 - 421

16
[ 1481-27-2 ]
[ 100-39-0 ]
[ 106245-03-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 80℃; for 1.5h;	To a stirred suspension of 2?-hydroxy-4?-fluoroacetophenone (16) (15 g,97.3 mmol) and K2CO3 (20.2 g, 146 mmol) in DMF (162 mL) was added benzyl bromide (18.3 g, 107 mmol) in a dropwise fashion at 0 C. The reaction mixture was stirred at 80 C for 1.5 h. After the completion of the reaction, the reaction mixture was allowed to cool to room temperature, and then filtered through a pad of Celite and rinsed with EtOAc (300 mL). The filtrate was washed with water (300 mL) and brine (50 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give the title compound (23.7 g, 99%) as colorless crystals.
99%	With potassium carbonate; In acetone; at 20℃; for 24h;	A mixture of 4-fluoro-2-hydroxyacetophenone (319 mg, 2.07 mmol), benzylbromide (0.29 mL, 2.48 mmol), K2CO3 (572 mg, 4.14 mmol) and acetone (12 mL) was stirred at rt for 24 h and filtered. The filtrate was concentrated and the residue purified by chromatography to give the sub-title compound (501 mg, 2.05 mmol, 99 %).
98%	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 70℃; for 1.5h;Inert atmosphere;	Benzyl bromide (1.03 g, 6.00 mmol) was added to a N,N-dimethylformamide solution (5 ml) of 1-(4-fluoro-2-hydroxyphenyl)ethanone (770 mg, 5.00 mmol) and potassium carbonate (860 mg, 5.00 mmol), at room temperature, under nitrogen stream, and stirring was carried out at 70C for 1.5 hours. The reaction solution was poured into a 2N aqueous hydrochloric acid solution, followed by extraction with ethyl acetate. The extract was washed sequentially with water and saline, and then the resulting organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated and the resulting residue was purified by silica gel column chromatography to afford 1-[2-(benzyloxy)-4-fluorophenyl]ethanone (1.20 g, yield 98%) as a white solid. 1H-NMR (CDCl3, 400 MHz) delta: 7.83 (1H, dd, J=8.0 Hz, 7.2 Hz), 7.44-7.39 (5H, m), 6.76-6.70 (2H, m), 5.15 (2H, s), 2.58 (3H, s).

With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;

Preparation 491 -[2-(BENZYLOXY)-4-FLUOROPHENYL]ETHANONEA mixture of 1 -(4-fluoro-2-hydroxyphenyl)ethanone (2.7 g,17.5 mmol), benzylbromide (3.60 g, 21.0 mmol) and K2CO3 (3.63 g, 26.3 mmol) was stirred in dry DMF (15 ml) under N2 at 8O C overnight. The solution was brought to ambient temperature and water and EtOAc was added. The water phase was extracted with EtOAc. The combined organic phases were washed with LiCI (5%) and evaporated to dryness to give the crude title compound (4.5 g). MS m/z (rel. intensity, 70 eV) 244 (M+, 18), 139 (9), 92 (17), 91 (bp), 65 (26).

Reference： [1]Synthesis,2017,vol. 49,p. 2074 - 2080
[2]Patent: WO2019/53426,2019,A1 .Location in patent: Page/Page column 65; 66
[3]Patent: EP2258697,2010,A1 .Location in patent: Page/Page column 83
[4]Patent: WO2009/133109,2009,A1 .Location in patent: Page/Page column 55

17
[ 1481-27-2 ]
[ 105-58-8 ]
[ 2145-27-9 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of l-(4-fluoro-2-hydroxyphenyl)ethanone (50 g, 0.33 mol) in toluene wasadded over 30 min to a suspension of NaH (60% oil, 65 g, 1.63 mol) in toluene. Then diethylcarbonate(59 mL, 0.49 mol) was added over 15 min and the reaction mixture was stirred at 115 C for 6 h. Themixture was cooled to rt followed by the addition of HC12N and diluted with EtOAc. The organicphase was washed with brine, dried over Na2SO4 and evaporated. The residue was purified bytrituration in hexane and Et2O to give the title compound.
		In a 250 mL two-neck round-bottom flask, 9 mmol of ohydroxyacetophenonein 15 mL toluene was slowly added to sodiumhydride (60% w/w suspension, 5 equiv, 45 mmol, 1.8 g) intoluene (10 mL) under N2 atmosphere at 0 C. After 15 min,13.5 mmol of diethyl carbonate in 10 mL toluene was added dropwise,and the mixture was stirred at room temperature for 30 minand refluxed until the reaction finished (monitored by TLC (ThinLayer Chromatography)). After the mixture cooled to room temperature,the reaction was quenched by slowly addition of 2 N hydrochloricacid. The resulting precipitate was further purified by ashort silica gel column chromatography to give a white solid.

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 13985 - 13997
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 7142 - 7156
[3]Patent: WO2004/108720,2004,A1 .Location in patent: Page 61
[4]Tetrahedron,2018,vol. 74,p. 970 - 974

18
[ 1481-27-2 ]
[ 616-38-6 ]
[ 1204755-16-7 ]

Yield	Reaction Conditions	Operation in experiment
64%		EXAMPLE 9-1; Preparation of racemic 2-(3,4-dichlorophenyl)-7-fluoro-2H-chromene-3- carboxylic acid; [00162] Step 1. A 1.0 M tetrahydrofuran solution of lithium bis(trimethylsilyl)amide (39.0 mL, 39.0 mmol) was stirred at -78 0C and treated over a 25 min period with a solution of l-(4-fluoro-2-hydroxyphenyl)ethanone (2.00 g, 13.0 mmol) in 50 mL of tetrahydrofuran. The resulting solution was stirred at -78 0C for 1 h, and then at -15 0C for 2 h. After being cooled again to -78 0C, the solution was treated with a solution of dimethyl carbonate (1.20 mL, 14.3 mmol) in tetrahydrofuran (5 mL). The resulting mixture was allowed to warm to rt where it stirred overnight. After this time, the mixture was poured over ice and then concentrated hydrochloric acid (10 mL) was added. The resulting mixture was extracted three times with dichloromethane. The combined organic phases were washed twice with water, dried over sodium sulfate and then concentrated under vacuum to yield a residue. The residue was purified by radial thin-layer chromatography (silica gel, 2-40% ethyl acetate-hexane) to provide methyl 3-(4- fluoro-2-hydroxyphenyl)-3-oxopropanoate as a white solid (1.76 g, 64%). 1H NMR (400 MHz, CDCl3) delta ppm 3.78 (s, 3 H) 3.98 (s, 2 H) 6.62 - 6.71 (m, 2 H) 7.69 (dd, J=8.9, 6.4 Hz, 1 H) 12.15 (d, J=1.5 Hz, 1 H). Mass spectrum m/z 213.14 (M+H)+.

Reference： [1]Patent: WO2010/9069,2010,A1 .Location in patent: Page/Page column 50-51

19
[ 1481-27-2 ]
[ 123-11-5 ]
[ 392-08-5 ]

Yield	Reaction Conditions	Operation in experiment
		5.2.1. General method 5.2.1.1. 5,7-Difluoro-3',4'-dimethoxyflavonolSodium ethoxide (1.19 g, 17.44 mmol) was dissolved in ethanol (20 mL) and cooled to room temperature. To this solution was added 4',6'-difluoro-2'-hydroxyacetophenone (1.0 g, 5.81 mmol) and this was stirred at room temperature for 1 h. 3,4-Dimethoxybenzaldehyde (0.96 g, 5.81 mmol) was then added and stirred at room temperature overnight. The resulting yellow suspension was poured into H2O (50 mL) and acidified to pH 1 with HCl (10% aq.). The yellow precipitate was filtered, washed with H2O and dried. Conversion and product verification was by TLC (SiO2, ethyl acetate/Pet. ether (40-60 C) (1:2)) and ESI-MS. This chalcone (1.4 g, 4.37 mmol) was suspended in methanol (50 mL), and NaOH (3 M aq.) (7.5 mL) was added to produce a yellow solution, which was cooled to 0 C. To this was added H2O2 (30% aq.) (1.90 mL, 16.76 mmol) and the solution stirred at 0 C for 3 h then overnight at room temperature if the reaction was not complete (by TLC). The resulting suspension was poured into HCl (10% aq.) (50 mL), extracted with CHCl3 or CH2Cl2 (3 × 30 mL), dried (MgSO4) and evaporated to yield a yellow solid which was recrystallised from ethanol or ethanol/methanol to yield yellow crystals of 5,7-difluoro-3',4'-dimethoxyflavonol (372 mg, 26% (from benzaldehyde)).

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2015,vol. 30,p. 484 - 491
[2]Synthetic Communications,2010,vol. 40,p. 944 - 950
[3]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 1273 - 1279
[4]European Journal of Medicinal Chemistry,2012,vol. 54,p. 952 - 958

20
[ 29866-54-4 ]
[ 1481-27-2 ]
[ 1235986-58-9 ]

Reference： [1]Journal of Combinatorial Chemistry,2010,vol. 12,p. 687 - 695

21
[ 1481-27-2 ]
[ 1268629-01-1 ]

Yield	Reaction Conditions	Operation in experiment
35%	With sulfuric acid; nitric acid; at 0℃; for 0.5h;	R4 - To a solution of cone. H2SO4 (400 mL) was added R3 (100 g, 0.65 mmol) at 0 C. Cone. HNO3 (66 mL) was added to the mixture dropwise at 0 C during 30 min. After addition, ice-water (2L) was added. The mixture was extracted with EtOAc (500 mL x 2). The combined organic layer was washed with brine (1000 mL), dried over Na2SO4 and evaporated in vacuum to give the residue which was purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate =10/1-3/1) to give R 7 (45 g, yield 35%) as a yellow solid. 1H NMR (CDC13, 400 MHz): d (ppm) 2.67 (s, 3H), 6.77-6.83 (t, J = 9.0 Hz, 1H), 7.90-7.95 (dd, J = 9.0, 6.3 Hz, 1H), 13.30 (s, 1H).
28%	With sulfuric acid; nitric acid; at 0℃; for 0.5h;	To <strong>[1481-27-2]1-(4-fluoro-2-hydroxyphenyl)ethan-1-one</strong> (0301-20) (1.0 g, 6.49 mmol, 1.0 eq.) at 0 CAdd 70% nitric acid (0.5 ml, 7.14 mmol, 1.1 equivalents) to a solution of 82% sulfuric acid (9 ml).The reaction was carried out at 0 C for half an hour.Pour the reaction solution into ice water (100 ml).Extracted with dichloromethane (50 ml x 2), the organic phase was dried,The residue was purified by silica gel column chromatography(eluent: petroleum ether: ethyl acetate = 10:1)The product was obtained as a pale yellow solid, 1-(4-fluoro-2-hydroxy-3-nitrophenyl)ethan-1-one (0.36 g, yield: 28%).
27%	With sulfuric acid; nitric acid; In water; at 0℃; for 0.516667h;	A mixture of 1-(4-fluoro-2-hydroxy-phenyl)ethanone (2332 mg, 15.13 mmol) in a pre- prepared solution of cone, sulphuric acid : water (8:2) (10 ml_) was prepared at rt and cooled to 0C. nitric acid (1634 mg, 18.16 mmol) (70%) was then added dropwise over 1 min and the mixture stirred for 30 mins at 0C and then poured into ice water (ca. 200 ml_) and the mixture extracted with ethyl acetate (2 x 200 ml_) and the organics dried over magnesium sulphate and concentrated under reduced pressure. The mixture was then purified by column chromatography (0-50% ethyl acetate/heptane) to afford 1-(4- fluoro-2-hydroxy-3-nitro-phenyl)ethanone (850 mg, 4.10 mmol), 27 % yield as a pale yellow solid. 1H NMR (400 MHz, CDCI3) delta 13.29 (d, J=1.4 Hz, 1 H), 7.92 (dd, J=5.8, 9.0 Hz, 1 H), 6.81 (dd, J=8.9, 8.9 Hz, 1 H), 2.67 (s, 3H); LCMS m/z 200 (M+H)+

With sulfuric acid; nitric acid; at 0℃; for 0.5h;

Intermediate 30. 1 -(4-fluoro-2-hydroxy-3-nitrophenyl)ethanoneA mixture of 1-(4-fluoro-2-hydroxyphenyl)ethanone (1000 mg, 6.49 mmol, Aldrich) and 82% sulfuric acid (9 ml.) was stirred vigorously and cooled to 0 0C. 70% Nitric acid (0.5 ml_, 7.83 mmol) was added dropwise. The mixture was stirred for 30 min. It was poured in to ice / water (100 ml.) and extracted with EtOAc (2 x 50 ml_). The combined organic layers were dried over sodium sulfate, filtered and evaporated to give an off-white solid. Mass: 1.16 g. This was purified by Biotage (4OM silica cartridge; eluent A / B 0 to 20%; A = 1% acetic acid in isohexane; B = 1 % acetic acid in EtOAc; collection by UV trigger). Impure fractions from this column were combined and re-purified using the same protocol. The output from both of the columns was combined to give the target compound (0.49 g) as a yellow solid, m/z [M-H]": 197.9. Retention time 0.93 min (LC/MS method 3).

Reference： [1]Patent: WO2020/33604,2020,A1 .Location in patent: Page/Page column 30
[2]Patent: CN108658908,2018,A .Location in patent: Paragraph 0188; 0189
[3]Patent: WO2017/221002,2017,A1 .Location in patent: Page/Page column 169
[4]Patent: WO2011/23753,2011,A1 .Location in patent: Page/Page column 81

22
[ 1481-27-2 ]
[ 100-44-7 ]
[ 106245-03-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate In diethyl ether for 6h; Reflux;

Reference： [1]Location in patent: experimental part Khlebnikova; Piven; Khripach; Lakhvich [Chemistry of Natural Compounds, 2011, vol. 47, # 1, p. 33 - 37]

23
[ 1481-27-2 ]
[ 1247949-34-3 ]

Yield	Reaction Conditions	Operation in experiment
25%	With ammonia; In methanol; at 0 - 20℃; for 2h;	[0489] Compound 67a: To a stirred solution of 4'-fluoro-2'-hydroxyacetophenone (2 g, 12.98 mmol) in methanol (10 mL) was added 7N ammonia in methanol (10 mL) at 0 C and the reaction mixture was stirred at room temperature for 2 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was concentrated under reduced pressure to afford 5-fluoro-2-(l-iminoethyl)phenol (67a; 0.5 g, 25%) as off white solid. (0859) [0490] 1H NMR (400 MHz, DMSO-d6) delta 2.47 (s, 3 H), 6.18 - 6.24 (m, 2 H), 7.48 - 7.55 (m, 1 H), 10.33 (br s, 1 H), 15.14 (brs, 1 H).
	With ammonia; In methanol; at 20℃; for 2h;	1 -(4-fluoro-2-hydroxyphenyl)ethan- 1-one (1.0 g, 6.49 mmol) in 7 M ammonia in MeOH (4.6 ml, 32.4 mmol) was stirred at ambient temperature for 2 h to give a yellow slurry.The slurry was filtered and the cake was dried to afford5-fluoro-2-(1-iminoethyl) phenol (466 mg, yield 47%) as bright yellow solid, which was used in the next step without thrther purification.

Reference： [1]Patent: WO2019/152731,2019,A1 .Location in patent: Paragraph 0489-0490
[2]Organic Letters,2011,vol. 13,p. 6300 - 6303
[3]Patent: US10259800,2019,B2 .Location in patent: Page/Page column 78; 80

24
[ 1481-27-2 ]
[ 68-12-2 ]
[ 69155-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; at 0 - 64℃; for 4h;	General procedure: To a cooled (0C)solution of 2'-hydroxyacetophenone (1 g, 1 eq) in DMF (30 mL) was added phosphorusoxychloride (5 eq). The mixture stirred at 64 C for 4 h until the 2'-hydroxyacetophenone consumed completely (TLC). The reaction was quenched withglacial water (100 mL), and the mixture stirred for an additional 30 mins. Then themixture was extracted three times with dichloromethane (100 mL). And then the solventwas evaporated in vacuo and the crude product was purified by column chromatographyon silica gel.

Reference： [1]Acta poloniae pharmaceutica,2013,vol. 70,p. 221 - 228
[2]Organic Letters,2019
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3034 - 3042
[4]Chemical Communications,2019,vol. 55,p. 202 - 205
[5]Molecules,2019,vol. 24

25
[ 1481-27-2 ]
[ 100-51-6 ]
[ 1300624-80-9 ]

Yield	Reaction Conditions	Operation in experiment
47%	With tert.-butylhydroperoxide; copper diacetate; In water; dimethyl sulfoxide; at 80℃; for 20h;Sealed tube;	General procedure: To an oven-dried sealed tube charged with 2-hydroxyacetophenone (1a) (40.8mg, 0.3mmol, 1.0equiv), Cu(OAc)2 (2.7mg, 0.015mmol, 5mol%), and TBHP (70% in water) (0.16mL, 1.2mmol, 4.0equiv) in DMSO (1mL, 0.3M) was added benzyl alcohol (2a) (65.4mg, 0.6mmol, 2equiv). The reaction mixture was allowed to stir at 80C for 20h. After cooling at room temperature, the reaction mixture was evaporated onto silica gel. Purification of the product by column chromatography (SiO2: n-hexanes/EtOAc=40:1) provided 3a (50.5mg) in 70% yield 4.2.4 2-Acetyl-5-fluorophenyl benzoate (3d) Colorless oil; Rf=0.55 (n-hexanes/EtOAc=6:1); 1H NMR (700 MHz, CDCl3) delta 8.18 (d, J=8.3 Hz, 2H), 7.89 (t, J=7.7 Hz, 1H), 7.64 (t, J=7.5 Hz, 1H), 7.51 (t, J=8.1 Hz, 2H), 7.06-7.05 (m, 1H), 6.97 (d, J=8.8 Hz, 1H), 2.50 (s, 3H); 13C NMR (175 MHz, CDCl3) delta 195.8, 164.9 (d, JC-F=255.9 Hz), 164.7, 151.1 (d, JC-F=11.3 Hz), 134.0, 132.3 (d, JC-F=10.5 Hz), 130.3, 128.8, 128.7, 127.6 (d, JC-F=3.0 Hz), 113.4 (d, JC-F=21.2 Hz), 111.8 (d, JC-F=24.4 Hz), 29.7; IR (KBr) nu 2923, 1746, 1688, 1603, 1452, 1357, 1263, 1149, 1023, 976 cm-1; HRMS (EI) Calcd for C15H11FO3 [M]+ 258.0692, found 258.0695.

Reference： [1]Tetrahedron,2013,vol. 69,p. 9391 - 9397

26
[ 1481-27-2 ]
[ 2923-94-6 ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium azide; iodine; sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; for 2h;

Reference： [1]Rajendar; Kant, Ruchir; Narender [Advanced Synthesis and Catalysis, 2013, vol. 355, # 18, p. 3591 - 3596]

27
[ 100-02-7 ]
[ 1481-27-2 ]
[ 1632055-79-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In water; acetonitrile; at 20℃; for 16h;Schlenk technique;	General procedure: In a 15 mL reaction tube a mixture of 2-acetylphenol (1a, 68mg, 0.5 mmol), 4-nitrophenol (2a, 174 mg, 1.25 mmol), t-BuOOH (70% in H2O, 2 mmol), TBAI (55 mg, 0.15 mol) in MeCN (2.0 mL) was stirred at r.t. under air for 16 h, until complete consumption of starting material as monitored by TLC. After the reaction was finished, the mixture was quenched with sat. Na2S2O3 solution, then extracted with EtOAc, dried over anhydrous Na2SO4, and evaporated in vacuum. The residue was purified by flash column chromatography on silica gel (PE-EtOAc, 8:1) to give the product 3a.

Reference： [1]Synlett,2014,vol. 25,p. 843 - 846

28
[ 1481-27-2 ]
[ 1613044-64-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(II) oxide; In dimethyl sulfoxide; at 100℃; for 2h;Sealed tube;	General procedure: A sealed tube was charged with 1-(2-hydroxyphenyl)ethanone 3a (75.1mg, 0.5mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (38.1mg, 0.25mmol), copper(II) oxide (20mg, 0.25mmol) and iodine (63.5mg, 0.25mmol) at room temperature, and then dried solvent DMSO (3mL) was added. The resulting mixture was stirred at 100C and monitored to completion by TLC analysis. After cooling to room temperature, H2O (50mL) was added and the aqueous mixture was extracted with EtOAc three times (3×50mL). The combined organic extracts were washed with brine (20mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel using petroleum ether/EtOAc as the eluent to give the expected product 4a as light yellow solid (72% yield).

Reference： [1]Tetrahedron,2014,vol. 70,p. 4331 - 4335

29
[ 542-69-8 ]
[ 124-38-9 ]
[ 1481-27-2 ]
4-butoxy-7-fluoro-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		General procedure: Similarly as described in our previous paper (Catal. Sci. Technol. 2014, 4, 1570), a 20 mLoven-dried autoclave containing a stirring bar was charged with o-hydroxyacetophenone (1)(0.5 mmol), DBU (1.0 mmol), and 2 mL dry DMSO. After purging the autoclave with CO2three times, the sealed autoclave was pressurized to the appropriate pressure with CO2. Thereaction mixture was stirred at 80 C for 24 h, then the autoclave was cooled to roomtemperature and the remaining CO2 was vented slowly. Then n-BuI (1.0 mmol) was addedinto the autoclave and the reaction mixture was stirred at 80 C for 4 h. The reaction mixturewas then diluted with water (30 mL) and extracted with ethyl acetate (3 × 30 mL). Thecombined organic layers were washed with water and brine, dried over Na2SO4 and filtered.The solvent was removed under vacuum. The product was isolated by columnchromatography on silica gel (hexane/ethyl acetate 2:1).

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 906 - 912

30
[ 1481-27-2 ]
[ 775-15-5 ]
1-(2-((1-benzylpyrrolidin-3-yl)oxy)-4-fluorophenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.7 g	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 20℃; for 3h;	A) 1-(2-((1-benzylpyrrolidin-3-yl)oxy)-4-fluorophenyl)ethanone A mixture of 1-benzylpyrrolidin-3-ol (4.1 g), 1-(4-fluoro-2-hydroxyphenyl)ethanone (3.0 g), triphenylphosphine (7.7 g), diisopropyl azodicarboxylate (40% toluene solution) (15 mL) and THF (50 mL) was stirred at room temperature for 3 hr. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.7 g). 1H NMR (300 MHz, CDCl3) delta 1.95-2.10 (1H, m), 2.26-2.43 (1H, m), 2.56-2.68 (4H, m), 2.72-2.83 (2H, m), 3.01 (1H, dd, J=10.5, 6.0 Hz), 3.60-3.74 (2H, m), 4.83-4.94 (1H, m), 6.52 (1H, dd, J=10.9, 2.3 Hz), 6.62-6.72 (1H, m), 7.28-7.37 (5H, m), 7.81 (1H, dd, J=8.7, 6.8 Hz).

Reference： [1]Patent: US2016/24049,2016,A1 .Location in patent: Paragraph 0802; 0803

31
[ 39931-77-6 ]
[ 1481-27-2 ]
7-fluoro-2-pyridin-4-ylmethylchromen-4-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2468 - 2477

32
[ 1481-27-2 ]
[ 105258-93-3 ]
benzyl 3-(2-(4-fluoro-2-hydroxyphenyl)-2-oxoethyl)-3-hydroxyazetidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.5%		Example 100A benzyl 3 -(2-(4-fluoro-2-hydroxyphenyl)-2-oxoethyl)-3-hydroxyazetidine-l -carboxylate A solution of diisopropylamine (1.573 mL, 11.04 mmol) in tetrahydrofuran (11 mL) was cooled to -10 C, treated dropwise with 2.5 M n-BuLi in hexanes (4.41 mL, 11.04 mmol), stirred at -10 C for 5 minutes, treated dropwise with a solution of 4'-fluoro-2'-hydroxyacetophenone (0.81 g, 5.26 mmol) in tetrahydrofuran (5 mL), stirred between -10 C and 0 C for 1 hour, cooled to - 60 C, treated dropwsie with a solution of benzyl 3-oxoazetidine-l -carboxylate (1.402 g, 6.83 mmol) in tetrahydrofuran (5 mL) over 15 minutes, stirred between - 60 C and - 50 C for 10 minutes, treated with a 10 % aqueous solution of KH2P04 (50 mL) and allowed to warm to room temperature. The mixture was extracted with ethyl acetate (twice). The combined ethyl acetate layers were washed with brine, dried (MgS04), filtered, concentrated, and chromatographed on silica gel eluted with a gradient of 20 % - 100 % ethyl acetate in heptanes to provide the title compound (1.35 g, 3.76 mmol, 71.5 % yield). 1H NMR (400 MHz, CDC13) delta ppm 12.08 (s, 1H), 7.72 (dd, J= 8.8, 6.3 Hz, 1H), 7.40 - 7.26 (m, 5H), 6.71 - 6.63 (m, 2H), 5.10 (s, 2H), 4.11 (d, J= 9.5 Hz, 2H), 3.95 (d, J= 9.4 Hz, 2H), 3.79 (s, 1H), 3.50 (s, 2H); MS (ESI) m/z 342 (M+H)+.

Reference： [1]Patent: WO2016/69757,2016,A1 .Location in patent: Page/Page column 199-200

33
[ 1481-27-2 ]
[ 105258-93-3 ]
benzyl 7'-fluoro-4'-oxospiro[azetidine-3,2'-chroman]-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/69757,2016,A1

34
[ 1481-27-2 ]
[ 31338-67-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfur; toluene-4-sulfonic acid / water / 8 h / 125 - 135 °C 2: sodium hydroxide; benzyltrimethylammonium chloride / water / 8 h / 100 °C

Reference： [1]Neyyappadath, Rifahath M.; Cordes, David B.; Slawin, Alexandra M. Z.; Smith, Andrew D. [Chemical Communications, 2017, vol. 53, # 17, p. 2555 - 2558]

35
[ 1481-27-2 ]
[ 4114-31-2 ]
2-hydroxy-4-fluoroacetophenone ethoxycarbonylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride; In ethanol; at 80℃; for 2h;	General procedure: A stirred solution of compound 2-Hydroxy-4-substitutephenylethanone,ethoxycarbonylhydrazine(1.1 equivalents) and concentrated HCl (0.08 equivalents) inethanol was boiled for 2 h(monitoring by TLC following the consumption of the initialcompound) and left at RT overnight .The separated precipitate was filtered off, washed withethanol, and dried in air.

Reference： [1]Molecules,2017,vol. 22

36
[ 10287-53-3 ]
[ 1481-27-2 ]
(Z)-3-(4-(dimethylamino)phenyl)-1-(4-fluoro-2-hydroxyphenyl)-3-hydroxyprop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium hydride In tetrahydrofuran at 60℃;

Reference： [1]Li, Jinbiao; Wu, Yishi; Xu, Zhenzhen; Liao, Qing; Zhang, Haihua; Zhang, Yi; Xiao, Lu; Yao, Jiannian; Fu, Hongbing [Journal of Materials Chemistry C, 2017, vol. 5, # 46, p. 12235 - 12240]

37
[ 383176-01-0 ]
[ 1481-27-2 ]
6-fluoro-4'-hydroxy-3',5'-dimetoxyflavone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		LiHMDS (1.0M in THF, 4.88 mmol) was added to a solution of methyl 4-O-tert-butyldimethylsilyl-3,5-dimethoxybenzoate(0.61 mmol) and fluorinated acetophenone (4?-fluoro-2?-hydroxyacetophenone or 5?-fluoro-2?-hydroxyacetophenone) in THF (10 ml). After stirring at room temperature for 24 h, the resultant solution was poured into 10% HCl aqueous solution, partitioned with EtOAc twice, and washed with brine. The organic layer was dried over anhydrous Na2SO4, concentrated, and vacuumed overnight. The residue was dissolved in 0.5% H2SO4 in AcOH and the acidic solution was stirred at 100 C for 3 h. The reactant was poured into distilled water, partitioned with EtOAc twice, and washed with brine. The organic layer was dried over anhydrous Na2SO4, concentrated in vacuo.The residue was purified using silica gel column chromatography eluted with CHCl3/MeOH (100/1), to afford 6F-tricin (52% yield) or 7F-tricin(71% yield).2.2.1. 6-Fluoro-4?-hydroxy-3?,5?-dimetoxyflavone (6F-tricin) Yellow amorphous powder, HRESITOFMS m/z 315.0663 [M - H]-(calcd for C17H12O5F, 315.0669); 1H NMR (400 MHz, DMSO-d6): delta 9.33(br s, 1H), 7.93 (dd, 1H, J=9.2 and 4.1 Hz), 7.77-7.68 (m, 2H), 7.41(s, 2H), 7.11 (s, 1H), 3.91 (s, 6H); 13C NMR (100 MHz, DMSO-d6): delta176.8, 163.8, 159.5 (JFC=991.9 Hz), 157.9, 148.7 (2C), 140.3, 125.0(JFC=30.6 Hz), 121.0, 115.7 (JFC=95.3 Hz), 109.8 (JFC=95.4 Hz),105.3, 104.9 (2C), 56.9 (2C).

Reference： [1]Antiviral Research,2018,vol. 154,p. 10 - 16

38
[ 5292-43-3 ]
[ 1481-27-2 ]
tert-butyl 2-(2-acetyl-5-fluorophenoxy)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate; In acetonitrile; at 80℃; for 2h;Inert atmosphere;	To a solution of 1.00 g (6.49 mmol) of 4'-fluoro-2'-hydroxyacetophenone in 15 ml of acetonitrile, 1.20 ml (8.18 mmol) of tert-butyl bromoacetate and 1.40 g (10.1 mmol) of potassium carbonate were added with stirring in an argon atmosphere and then reacted at 80 C. for 2 hours. After completion of the reaction, the cooled reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed twice with water, then dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. n-Hexane was added to the obtained concentration residue and concentrated under reduced pressure again. n-Hexane was added to the obtained concentration residue and then ultrasonicated, and the deposited solid was collected by filtration. The obtained solid was washed with n-hexane and dried under reduced pressure at room temperature to obtain 1.45 g of the title compound (yield: 83%) as a white solid. Mass spectrum (CI, m/z): 269 [M+1]+. 1H-NMR spectrum (400 MHz, CDCl3) delta: 7.84 (dd, J=7.0, 8.8 Hz, 1H), 6.74 (ddd, J=2.3, 7.7, 8.8 Hz, 1H), 6.53 (dd, J=2.3, 10.5 Hz, 1H), 4.60 (s, 2H), 2.70 (s, 3H), 1.50 (s, 9H).

Reference： [1]Patent: US2018/186818,2018,A1 .Location in patent: Paragraph 1259; 1260; 1261; 1262; 1263

39
[ 1481-27-2 ]
[ 105-58-8 ]
ethyl 3-(4-fluoro-2-hydroxyphenyl)-3-oxopropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		General procedure: Under a dry argon atmosphere, lithium bis(trimethylsilyl)amide (1 M, 3 mmol) was cooled 78 C and a mixture of 2-hydroxyacetophenone (136 mg, 1 mmol) in dry THF (2 mL) was added dropwise to the above solution in 20 min. The reaction solution was stirred at 78 C for 1 h and in ice-bath for 2 h, and then a solution of diethyl carbonate (127.4 mg, 1.08 mmol) in dry THF(1 mL) was rapidly added to the above mixture in ice-bath for 3-4 h. Then, the mixture was stirred at room temperature. After 2-hydroxyacetophenone had disappeared completely, the reaction solution poured into a mixture of concentrated HCl (1.5 mL) and ice (20 g). The mixture was extracted with CHCl3. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude products were purified using column chromatography on silica gel to give 1a in good yields, and 1b-1s were prepared with the same method.

Reference： [1]Tetrahedron,2018,vol. 74,p. 4712 - 4720

40
[ 14527-42-5 ]
[ 1481-27-2 ]
1-(4-fluoro-2-hydroxyphenyl)-3-(thiazol-2-yl)propane-1,3-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 8468 - 8473

41
[ 1481-27-2 ]
[ 75-08-1 ]
1-(4-(ethylthio)-2-hydroxyphenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		To sodium hydroxide (135mg, 3.38mmol, 1.3 equivalents)Ethyl mercaptan (0.24 mL, 3.38 mmol, 1.3 eq.) was added to a solution of water (1 ml).The mixture was stirred at room temperature for 30 minutes.Add a solution of 4-fluoro-2-hydroxyacetophenone (0.4 g, 2.60 mmol, 1.0 eq.) in dimethyl sulfoxide (5 ml).It was then heated to 120 C for 7 hours.The reaction solution was cooled to room temperature and diluted with water (30 mL).It was then extracted with ethyl acetate (30 mL x 3).The extract was washed with brine (20 mL × 1) and dried over anhydrous sodium sulfate.The crude product obtained by concentration was purified by silica gel column chromatography ( petroleum ether: ethyl acetate = 60:1)Purified to give a pale yellow oily liquid1-(4-(ethylthio)-2-hydroxyphenyl)ethan-1-one (228 mg, yield: 45%).

Reference： [1]Patent: CN108658908,2018,A .Location in patent: Paragraph 0310; 0311

42
[ 107-03-9 ]
[ 1481-27-2 ]
1-(2-hydroxy-4-(propylthio)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With sodium hydroxide; In propan-1-ol; water; dimethyl sulfoxide; at 120℃; for 5h;	To sodium hydroxide (156mg, 3.9mmol, 1.5 equivalents)To the solution of water (1 ml) was added propanol (0.35 mL, 3.9 mmol, 1.5 eq.).The mixture was stirred at room temperature for 30 minutes.Add a solution of 4-fluoro-2-hydroxyacetophenone (0.4 g, 2.60 mmol, 1.0 eq.) in dimethyl sulfoxide (5 ml).It was then heated to 120 C for 5 hours.The reaction solution was cooled to room temperature and diluted with water (30 mL).It was then extracted with ethyl acetate (30 mL x 3).The extract was washed with brine (30 mL × 1) and dried over anhydrous sodium sulfate.Concentrated crude product by silica gel column chromatography(petroleum ether: ethyl acetate = 60:1)Purified to give a pale yellow oily liquid1-(2-Hydroxy-4-(propylthio)phenyl)ethan-1-one (283 mg, yield: 52%).

Reference： [1]Patent: CN108658908,2018,A .Location in patent: Paragraph 0316; 0317

43
[ 79-01-6 ]
[ 1481-27-2 ]
(E)-1-(2-((1,2-dichlorovinyl)oxy)-4-fluorophenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate; In N,N-dimethyl-formamide; at 50 - 70℃; for 16h;Inert atmosphere;	General procedure: The 2-hydroxy acetophenones (4-7 mmol) were mixed with powdered K2CO3 (3 equiv.) in DMF (1.2 mL/mmol). The reaction mixture was then heated to 50C under nitrogen atmosphere. Trichloroethylene (neat, 3 equiv.) was then added dropwise through a syringe to the stirred reaction flask over 30 s. The reaction temperature was then raised to 70C and stirred for 16 h. After the reaction was judged complete (by TLC), the heating was stopped and reaction mixture allowed to cool to room temperature. The solvents were then evaporated under vacuum and the residue was partitioned between ethyl acetate and aqueous NaHCO3 solution. The layers were separated and the aqueous layer was extracted once with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The crude product thus obtained was purified by silica gel flash column chromatography (0-40% ethyl acetate in hexanes) to afford the corresponding 2-(1,2-dichlorovinyloxy) acetophenones.

Reference： [1]Tetrahedron,2018,vol. 74,p. 5715 - 5724

44
[ 120-57-0 ]
[ 1481-27-2 ]
3-(benzo[d][1,3]dioxol-5-yl)-1-(4-fluoro-2-hydroxyphenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium hydroxide; In ethanol; at 20℃; for 24h;	To a solution of piperonal (1, mmol) in 20 mL of ethanol with 4?-Fluoro-2?-hydroxyacetophenone (2, 10 mmol), 10 mL of 20% KOH wasadded and the reaction mixture was allowed to react at room temperaturefor 24 h. After the completion of the reaction monitored byTLC, the reaction mass was quenched by 30 mL of water and extractedwith 3×30 mL of chloroform followed by drying of the organic layerusing anhydrous sodium sulfate. The mass was then concentrated invacuum and purified by column chromatography with petroleumether:ethyl acetate to give 3 in 69% of yield. Yellowish brown solid,m.p. 167-169 C; 1H NMR (DMSO-d6, 400 MHz): delta 12.71 (s, 1H), 7.83(d, J=15.1 Hz, 1H), 7.67-7.44 (m, 6H), 7.39 (d, J=15.3 Hz, 1H),6.05 (s, 2H, CH2).2.2.

Reference： [1]Bioorganic Chemistry,2019,vol. 87,p. 23 - 30

45
[ 701-83-7 ]
[ 1481-27-2 ]
[ 98619-07-9 ]

Reference： [1]Synthetic Communications,2019,vol. 49,p. 576 - 586

46
[ 1481-27-2 ]
2-(3,9-difluoro-12-methyl-6H,12H-6,12-methanodibenzo[b,f][1,5]dioxocin-6-yl)-1-(4-fluoro-2-hydroxyphenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With pyrrolidine; In hexane; at 80℃; for 48h;Inert atmosphere; Molecular sieve;	General procedure: In a 10 mL round bottom flask equipped with a condenser, the corresponding 2?-hydroxyacetophenone (6.22 mmol) was heated in hexane (5 mL) for 5-10 min to dissolve completely, after which pyrrolidine (2.08 mmol, 0.33 equiv) and molecular sieves (3 A beads, 362 mg) were added while stirring under argon. The resulting mixture was refluxed at 80 C for 24-48 h and then allowed to cool to room temperature. After cooling to room temperatute (r. t.), ethyl acetate was added to the reaction mixture, followed by saturated NH4Cl (15 mL). The aqueous layer was extracted with ethyl acetate (3 x 20 mL) and the combined organic layers were dried over MgSO4, filtered out and the solvent was removed under reduced pressure. The residue was then purified by flash column chromatography on silica (Hexane:EtOAc 98:2) to give the desired product. 1H and 13C spectra of all compounds, 1-7 is available in the supplementary material.

Reference： [1]Molecules,2019,vol. 24

47
[ 5381-20-4 ]
[ 1481-27-2 ]
2-(benzo[b]thiophen-3-yl)-7-fluoro-3-hydroxy-4H-chromen-4-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 183

48
[ 5381-20-4 ]
[ 1481-27-2 ]
(E)-3-(benzo[b]thiophen-3-yl)-1-(4-fluoro-2-hydroxyphenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium hydroxide; In ethanol; water; at 20℃;	General procedure: An aqueous solution of NaOH (3M, 1.6mL) was added to a solution of aromatic ketone (1mmol) and 3-methoxybenzaldehyde (1.2 eq), in EtOH (1-2mL). The reaction was stirred at r.t for 18-24h. The reaction mixture was cooled in an ice-water bath and acidified to pH 2 with concentrated HCl (37%). The solid formed was filtered, washed with ethanol and then further purified by recrystallization from ethanol. When no precipitate occurred, the reaction mixture was extracted with dichloromethane and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Column chromatography was then utilized to purify the desired product.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 183

49
[ 398489-26-4 ]
[ 1481-27-2 ]
tert-butyl 3[2-(4-fluoro-2-hydroxyphenyl)-2-oxoethyl]-3-hydroxyazetidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%		To a solution of diisopropylamine (17.7 mL, 125 mmol) in THF (50 mL) cooled to -15 C, 2.5 M -BuLi in hexane (50 mL) was added dropwise under nitrogen atmosphere, and the mixture was stirred at -15 C for 30 minutes. Then a solution of 8.96 g (58. 14 mmol) of 4?- fluoro- T -hydroxy acetophenone in THF (50 mL) was added dropwise, and the mixture was stirred at - 15 C for 1 hour, and then treated with a solution of tert- butyl 3-oxoazetidine-l- carboxylate (12.9 g, 75.6 mmol) in THF (50 mL) dropwise for 20 minutes, allowed to warm to room temperature and stirred at this temperature for 1 hour. The reaction mixture was quenched by addition of saturated NHrCl solution (100 mL). The reaction mixture was extracted with ethyl acetate (2x90 mL), the combined organic layer was washed with brine (120 mL), dried over anhydrous NaiSOr, filtered and concentrated in vacuo. The residue was triturated with diisopropyl ether (50 mL), the precipitated white crystals were filtered off, washed with diisopropyl ether, and dried to yield 16.79 g (89 %) of the title compound

Reference： [1]Patent: WO2020/12422,2020,A1 .Location in patent: Page/Page column 41

50
[ 1481-27-2 ]
[ 134178-07-7 ]
7-fluoro-4'-hydroxy-3',5'-dimethoxyflavone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		In tetrahydrofuran (10 ml), 200 mg (0.61 mmol) of 4-O-tert-butyldimethylsilyl-3,5-dimethoxybenzoate and 188 mg (1.22 mmol) of 4?-fluoro-2?-hydroxyacetophenone were dissolved. To the solution thus obtained, 4.88 ml of a tetrahydrofuran solution of 1M lithium bis(trimethylsilyl)amide was added, followed by stirring at room temperature for one day. Then, 10% aqueous hydrochloric acid solution was added to the mixture thus obtained, and the mixture was extracted with ethyl acetate twice and washed with saturated saline, followed by drying over anhydrous sodium sulfate. After evaporating the solvent, the residue thus obtained was sufficiently dried using a vacuum pump overnight. Next, the solid thus obtained was dissolved in 0.5% sulfuric acid-containing acetic acid, and reacted at 100 C. for 3 hours. Distilled water was poured into the reactant thus obtained, and the reactant was extracted with ethyl acetate twice and washed with saturated saline, followed by drying over anhydrous sodium sulfate. After evaporating the solvent, the residue thus obtained was purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain 137 mg (yield of 71%) of 7-fluoro-4?-hydroxy-3?,5?-dimethoxyflavone. The results of NMR spectrum analysis are shown below. 1H NMR (400 MHz, DMSO-d6): delta9.33 (s, 1H, OH), 8.08 (dd, 1H, J=9.2 and 6.4 Hz, H-5), 7.80 (dd, 1H, J=10.1 and 2.8 Hz, H-8), 7.40-7.32 (m, 3H, H-2?, H-6 and H-6?), 7.09 (s, 1H, H-3),3.90 (s, 6H, 2OMe).

Reference： [1]Patent: US2020/79750,2020,A1 .Location in patent: Paragraph 0047-0048

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P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1481-27-2 ] {[proInfo.proName]}

Quality Control of [ 1481-27-2 ]

Related Doc. of [ 1481-27-2 ]

Product Details of [ 1481-27-2 ]

Calculated chemistry of [ 1481-27-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1481-27-2 ]

Application In Synthesis of [ 1481-27-2 ]

[ 1481-27-2 ] Synthesis Path-Upstream 1~4

[ 1481-27-2 ] Synthesis Path-Downstream 1~50

Related Functional Groups of [ 1481-27-2 ]

Fluorinated Building Blocks

Aryls

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1481-27-2 ]