[ CAS No. 54370-00-2 ] {[proInfo.proName]}

Name: 54370-00-2|(2-Bromo-4,5-dimethoxyphenyl)methanol|95+%
Brand: Ambeed
SKU: A155733
Rating: 90 (26 reviews)

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3d Animation Molecule Structure of 54370-00-2

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Quality Control of [ 54370-00-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 54370-00-2 ]

Product Details of [ 54370-00-2 ]

CAS No. :	54370-00-2	MDL No. :	MFCD02093896
Formula :	C₉H₁₁BrO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SDZSRNYOXRHPHZ-UHFFFAOYSA-N
M.W :	247.09	Pubchem ID :	618887
Synonyms :

Calculated chemistry of [ 54370-00-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	53.25
TPSA :	38.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.4
Log Po/w (XLOGP3) :	1.67
Log Po/w (WLOGP) :	1.81
Log Po/w (MLOGP) :	1.63
Log Po/w (SILICOS-IT) :	2.36
Consensus Log Po/w :	1.98

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.57
Solubility :	0.669 mg/ml ; 0.00271 mol/l
Class :	Soluble
Log S (Ali) :	-2.1
Solubility :	1.98 mg/ml ; 0.008 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.34
Solubility :	0.113 mg/ml ; 0.000456 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 54370-00-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 54370-00-2 ]

* 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 [ 54370-00-2 ]
Downstream synthetic route of [ 54370-00-2 ]

[ 54370-00-2 ] Synthesis Path-Upstream 1~3

1
[ 54370-00-2 ]
[ 5392-10-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 80℃; Schlenk technique	General procedure: In an oven dried Schlenk tube, were added alcohol 1 (69.0–199.5 mg, 0.5 mmol), CuI (10 molpercent)and 1,10-Phenanthroline (20 molpercent) and K3PO4 (2 mmol) followed by the addition of dioxane (2mL) at room temperature under open air atmosphere. The stirred reaction mixture was heated inan oil bath at 80 C for 7–48 h. Progress of the reaction was monitored by TLC till the reaction iscompleted. Then, the reaction mixture was cooled to room temperature, quenched with aqueousNH4Cl solution and then extracted with CH2Cl2 (3 10 mL). The organic layer was washed withsaturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reducedpressure and purification of the crude material by silica gel column chromatography (petroleumether/ethyl acetate) furnished the aldehyde/ketone 2 (61–97percent).
82%	at 55℃; for 1 h; Microwave irradiation	General procedure: The benzyl alcohols substrates (1a–1p) (0.2mmol), FeCl₃·6H₂O (0.002mmol, 5.4mg) and triphenylmethanol 2 (0.2mmol, 52mg) were mixed in a dried vessel. Then the reaction was irradiated under the microwave at 55°C for 1h. The crude mixture was purified by a flash column chromatography to afford the benzaldehydes (4a–4p).
69%	With tert.-butylhydroperoxide; N,N'-ortho-phenylene-bis(salicylideneiminato) copper(II); sodium hydroxide In water; acetonitrile at 20℃;	General procedure: Alcohol (0.5 mmol), salophen copper (II) complex (2 molpercent), NaOH (0.6 equiv), and 70percent TBHP in water (1.1 equiv) were dissolved in acetonitrile (5 mL), and the homogeneous solution was stirred at room temperature in air overnight. After completion of the reaction, the solvent was evaporated under reduced pressure. The residue was purified over silica gel by column chromatography (10–25percent EtOAc in hexane).

Reference： [1] Synthetic Communications, 2014, vol. 44, # 14, p. 2076 - 2087
[2] European Journal of Medicinal Chemistry, 2015, vol. 94, p. 149 - 162
[3] Tetrahedron, 2015, vol. 71, # 38, p. 6744 - 6748
[4] Synthetic Communications, 2015, vol. 45, # 11, p. 1334 - 1341

2
[ 54370-00-2 ]
[ 14140-15-9 ]
[ 1008355-81-4 ]
[ 5392-10-9 ]

Reference： [1] Journal of Chemical Research, 2006, # 11, p. 698 - 701

3
[ 54370-00-2 ]
[ 51655-39-1 ]

Reference： [1] Tetrahedron, 2003, vol. 59, # 52, p. 10581 - 10591
[2] Journal of the American Chemical Society, 1937, vol. 59, p. 1541,1545
[3] Chemical and Pharmaceutical Bulletin, 1974, vol. 22, # 9, p. 2108 - 2112

[ 54370-00-2 ] Synthesis Path-Downstream 1~102

1
[ 54370-00-2 ]
[ 54370-01-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; thionyl chloride; In chloroform; at 0 - 20℃;	Synthesis Example 8; Synthesis of 6-bromo-3,4-dimethoxy-benzyl chloride intermediate VIII; To a stirred solution of 6-bromoveratrumaldehyde (3 mmol, 1 eq.) in ethanol (10 mL) sodium borohydride (1 mmol, 4 eq.) was slowly added. The reaction was stirred for 2 hours and then the solvent was removed by rotary evaporation. The resulting white solid was treated with saturated ammonium chloride (15 mL). The aqueous was then extracted with chloroform, dried over magnesium sulfate, then removed by rotary evaporation to afford the alcohol (2.6 mmol, 87% yield). The alcohol (2 mmol, 1 eq.) was then stirred with pyridine (40 μL) in anhydrous chloroform (10 mL) to 0 C. Thionyl chloride (4 mmol, 2 eq.) was then added drop wise and the reaction was stirred at room temperature for 3 hours. The reaction progress was monitored by TLC. After complete consumption of starting material the reaction was poured into water (10 mL) and extracted with chloroform (1×20 mL). The organic layer was washed with H2O (2×10 brine (1×10 mL), dried over magnesium sulfate, filtered and evaporated to afford the benzyl chloride intermediate VIII (598 mg, 2 mmol, 100% yield). TLC (EtOAc/hexanes, 1:1) Rf=0.73; ESI-MS m/z=230.9 [M-Cl]+.
100%	With pyridine; thionyl chloride; In chloroform; at 0 - 20℃; for 3h;	To a stirred solution of 6-bromoveratrumaldehyde (3 mmol, 1 eq.) in ethanol (10 mL) sodium borohydride (1mmol, 4 eq.) was slowly added. The reaction was stirred for 2 hours and then the solvent was removed by rotaryevaporation. The resulting white solid was treated with saturated ammonium chloride (15 mL). The aqueous was thenextracted with chloroform, dried over magnesium sulfate, then removed by rotary evaporation to afford the alcohol (2.6mmol, 87% yield). The alcohol (2 mmol, 1 eq.) was then stirred with pyridine (40 mL) in anhydrous chloroform (10 mL)to 0 C. Thionyl chloride (4 mmol, 2 eq.) was then added drop wise and the reaction was stirred at room temperaturefor 3 hours. The reaction progress was monitored by TLC. After complete consumption of starting material the reactionwas poured into water (10 mL) and extracted with chloroform (1x 20 mL). The organic layer was washed with H2O (2 x10 mL), brine (1 x 10 mL), dried over magnesium sulfate, filtered and evaporated to afford the benzyl chloride intermediateVIII (598 mg, 2 mmol, 100% yield). TLC (EtOAc/hexanes, 1:1) Rf = 0.73; ESI-MS m/z = 230.9 [M-Cl]+.
	With thionyl chloride; In dichloromethane; at 20℃; for 0.5h;	(2-Bromo-4,5~dimethoxy-phenyl)-methanol (2.47g) is dissolved in methylene chloride (30ml) and thereto is added thionyl chloride (875μl) and, the mixture is stirred at room temperature for 30 minutes. The reaction <n="210"/>solution is concentrated under reduced pressure, and thereto is added to hexane and the resulting crystal is filtered to give l-bromo-2-chloromethyl- 4,5-dimethoxy-benzene (2.25g). MS (m/z): 229/231.

	With hydrogenchloride; In water; at 20℃; for 0.5h;	Step A: (2-Bromo-4,5-dimethoxy-phenyl)-methanol (25.09 g, 0.1015 mol) was added as a solid to a vigorously stirred solution of concentrated aqueous HCl (75 mL). The resulting white suspension was stirred at room temperature for 30 min. The resulting mixture was then extracted with CH2Cl2 (3×) and the combined extracts dried over MgSO4, filtered and concentrated in vacuo to yield 1-bromo-2-chloromethyl-4,5-dimethoxy-benzene as a white solid.
1.1 g	With thionyl chloride; In dichloromethane; at 20℃; for 3h;	A mixture of (2-bromo-4,5-dimethoxy-phenyl)methanol (1.0 g, 4.05 mmol) and SOd2(0.32 mL, 4.46 mmol) in DCM (10 mL) was stirred at rt for 3 brs. The reaction mixture was then concentrated to give 1-bromo-2-(chloromethyl)-4,5-dimethoxy-benzene (1.1 g) which was used in the next step without further purification.

Reference： [1]Patent: US2010/210593,2010,A1 .Location in patent: Page/Page column 45
[2]Patent: EP2942346,2015,A1 .Location in patent: Paragraph 0154
[3]Journal of Organic Chemistry,2000,vol. 65,p. 6398 - 6411
[4]Journal of the American Chemical Society,1937,vol. 59,p. 1541,1545
[5]Chemical and Pharmaceutical Bulletin,1974,vol. 22,p. 2108 - 2112
[6]Tetrahedron,2003,vol. 59,p. 10581 - 10591
[7]Patent: WO2007/88996,2007,A1 .Location in patent: Page/Page column 208-209
[8]Patent: US2011/105490,2011,A1 .Location in patent: Page/Page column 26
[9]Patent: WO2017/17043,2017,A1 .Location in patent: Page/Page column 21

2
[ 91-16-7 ]
[ 54370-00-2 ]
[ 25914-50-5 ]

Reference： [1]Archiv der Pharmazie,2012,vol. 345,p. 444 - 453
[2]Heterocycles,1992,vol. 33,p. 43 - 46

3
[ 5392-10-9 ]
[ 54370-00-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 20℃; for 0.333333h;	General procedure: Aldehyde 8a or 8b was dissolved in THF, methanol and 0.5 equiv of NaBH4 were added, and the mixture was stirred for 20 min at room tem-perature. The mixture was diluted with water, the organic solvents were removed under reduced pres-sure, and the aqueous phase was extracted with diethyl ether. The extract was dried over anhydrous Na2SO4 and evaporated under reduced pressure, and the residue was recrystallized from chloroform-petroleum ether. (2-Bromo-4,5-dimethoxyphenyl)metanol was synthesized from 0.53 g (3.2 mmol) of aldehyde 8a using 0.06 g (1.6 mmol) of NaBH4, 7 mL of THF, and 7 mL of methanol. Yield 0.51 g (97%), white crystals, mp 143C [22]. (2-Bromo-4,5-dimethoxyphenyl)metanol was synthesized from 0.53 g (3.2 mmol) of aldehyde 8a using 0.06 g (1.6 mmol) of NaBH4, 7 mL of THF, and 7 mL of methanol. Yield 0.51 g (97%), white crystals, mp 143C [22].
87%		Synthesis Example 8; Synthesis of 6-bromo-3,4-dimethoxy-benzyl chloride intermediate VIII; To a stirred solution of 6-bromoveratrumaldehyde (3 mmol, 1 eq.) in ethanol (10 mL) sodium borohydride (1 mmol, 4 eq.) was slowly added. The reaction was stirred for 2 hours and then the solvent was removed by rotary evaporation. The resulting white solid was treated with saturated ammonium chloride (15 mL). The aqueous was then extracted with chloroform, dried over magnesium sulfate, then removed by rotary evaporation to afford the alcohol (2.6 mmol, 87% yield). The alcohol (2 mmol, 1 eq.) was then stirred with pyridine (40 μL) in anhydrous chloroform (10 mL) to 0 C. Thionyl chloride (4 mmol, 2 eq.) was then added drop wise and the reaction was stirred at room temperature for 3 hours. The reaction progress was monitored by TLC. After complete consumption of starting material the reaction was poured into water (10 mL) and extracted with chloroform (1×20 mL). The organic layer was washed with H2O (2×10 brine (1×10 mL), dried over magnesium sulfate, filtered and evaporated to afford the benzyl chloride intermediate VIII (598 mg, 2 mmol, 100% yield). TLC (EtOAc/hexanes, 1:1) Rf=0.73; ESI-MS m/z=230.9 [M-Cl]+.
87%	With sodium tetrahydroborate; ethanol; for 2h;	To a stirred solution of 6-bromoveratrumaldehyde (3 mmol, 1 eq.) in ethanol (10 mL) sodium borohydride (1mmol, 4 eq.) was slowly added. The reaction was stirred for 2 hours and then the solvent was removed by rotaryevaporation. The resulting white solid was treated with saturated ammonium chloride (15 mL). The aqueous was thenextracted with chloroform, dried over magnesium sulfate, then removed by rotary evaporation to afford the alcohol (2.6mmol, 87% yield). The alcohol (2 mmol, 1 eq.) was then stirred with pyridine (40 mL) in anhydrous chloroform (10 mL)to 0 C. Thionyl chloride (4 mmol, 2 eq.) was then added drop wise and the reaction was stirred at room temperaturefor 3 hours. The reaction progress was monitored by TLC. After complete consumption of starting material the reactionwas poured into water (10 mL) and extracted with chloroform (1x 20 mL). The organic layer was washed with H2O (2 x10 mL), brine (1 x 10 mL), dried over magnesium sulfate, filtered and evaporated to afford the benzyl chloride intermediateVIII (598 mg, 2 mmol, 100% yield). TLC (EtOAc/hexanes, 1:1) Rf = 0.73; ESI-MS m/z = 230.9 [M-Cl]+.

	With sodium tetrahydroborate; In methanol; at 20℃; for 1h;Inert atmosphere;	General procedure: To an ice cold, magnetically stirred solution of a bromobenzaldehyde 7 (500 mg, 1.56-2.70 mmol) in methanol (15-20 mL), was added sodium borohydride (2.73-4.05 mmol). Then the reaction mixture was allowed to attain room temperature and stirred for 1 h. Solvent was removed under reduced pressure, treated with aqueous NH4Cl solution and extracted with ethyl acetate (3 ´ 15 mL). The organic layer was washed with saturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the filtrate under reduced pressure and purification of the crude material by silica gel column chromatography (petroleum ether/ethyl acetate) furnished the alcohol 1 (77-98%).
	With sodium tetrahydroborate; In dichloromethane; at 20℃; for 0.5h;	General procedure: To a solution of various benzaldehydes 4aew (10 mmol) dissolved in methanol (50 mL) was added sodium borohydride (20 mmol) at room temperature, and the mixturewas stirred at the same temperature for 30 min and concentrated under reduced pressure. The residue was diluted with methylene chloride (500 mL) and washed with water, and dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the corresponding crude phenylmethanols 5a-w
	With methanol; sodium tetrahydroborate; at 0℃; for 2.5h;	General procedure: To a stirring solution of 2,5-dimethoxyl benzaldehyde 1a (0.67 g, 4 mmol) dissolved in anhydrous methanol (30 mL) was added NaBH4 (0.84 g, 22 mmol) in batches at 0 ºC over a period of 0.5 h. The reaction mixture was stirred at the same temperature for 2 h. After removal of the methanol under reduced pressure, the residue was diluted with methylene chloride (30 mL), washed with distilled water (3 Χ 10 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude product 2a.

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 2599 - 2604
[2]Journal of Organic Chemistry,2007,vol. 72,p. 3293 - 3301
[3]Russian Journal of Organic Chemistry,2016,vol. 52,p. 1481 - 1489
Zh. Org. Khim.,2016,vol. 52,p. 1489 - 1496,8
[4]Synlett,2011,p. 2733 - 2739
[5]Organic Letters,2022,vol. 24,p. 256 - 261
[6]Tetrahedron Letters,2001,vol. 42,p. 6973 - 6975
[7]Patent: US2010/210593,2010,A1 .Location in patent: Page/Page column 45
[8]Patent: EP2942346,2015,A1 .Location in patent: Paragraph 0154
[9]Organic Letters,2021,vol. 23,p. 7285 - 7289
[10]Journal of Organic Chemistry,2000,vol. 65,p. 6398 - 6411
[11]European Journal of Organic Chemistry,2008,p. 196 - 213
[12]Journal of Organic Chemistry,1990,vol. 55,p. 1471 - 1475
[13]Journal of Organic Chemistry,1992,vol. 57,p. 2029 - 2033
[14]Tetrahedron,1995,vol. 51,p. 5341 - 5350
[15]Journal of Chemical Research,2006,p. 698 - 701
[16]Tetrahedron Letters,2012,vol. 53,p. 5635 - 5640
[17]European Journal of Medicinal Chemistry,2012,vol. 55,p. 125 - 136
[18]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5971 - 5975
[19]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2495 - 2502
[20]Tetrahedron,2013,vol. 69,p. 10098 - 10107
[21]Organic Letters,2014,vol. 16,p. 484 - 487
[22]Tetrahedron,2015,vol. 71,p. 8172 - 8177
[23]Organic and Biomolecular Chemistry,2017,vol. 15,p. 69 - 75
[24]Chemical Communications,2017,vol. 53,p. 8042 - 8045
[25]Organic Letters,2019,vol. 21,p. 170 - 174
[26]Angewandte Chemie - International Edition,2019,vol. 58,p. 6420 - 6424
Angew. Chem.,2019,vol. 131,p. 6486 - 6490,5

4
[ 54370-00-2 ]
[ 18162-48-6 ]
[ 137105-58-9 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 487 - 490
[2]Journal of the Chemical Society. Perkin transactions I,1993,p. 2599 - 2604
[3]European Journal of Organic Chemistry,2011,p. 1664 - 1681
[4]Organic Letters,2021,vol. 23,p. 7285 - 7289
[5]Journal of Organic Chemistry,2008,vol. 73,p. 7509 - 7516

5
[ 54370-00-2 ]
[ 74-88-4 ]
[ 124618-99-1 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 1664 - 1681
[2]European Journal of Organic Chemistry,2008,p. 196 - 213
[3]Journal of Organic Chemistry,1990,vol. 55,p. 1471 - 1475

6
[ 54370-00-2 ]
[ 53207-00-4 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus tribromide; In dichloromethane; at 0℃; for 0.5h;	General procedure: To a solution of phenylmethanols 5a-w (5 mmol) dissolved in methylene chloride (50 mL) in an ice-water bath was added phosphorus tribromide (5.5 mmol), and the mixture was stirred at the same temperature for 30 min. The mixture was washed with cool water, dried over anhydrous Na2SO4 and concentrated under reduced pressure to yield (bromomethyl)benzenes 6aew as offwhite solids or light yellow oils
	With phosphorus tribromide; In dichloromethane; at 0 - 5℃; for 0.75h;	General procedure: crude product 2a which was then dissolved in anhydrous methylene chloride (50 mL) and cooled to 0-5 ºC by ice bath. To this solution was added dropwise phosphorus tribromide (0.5 mL, 5 mmol) over a period of 15 min and stirred for 0.5 h at the same temperature, and then washed with saturated brine (3 Χ 15 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude compound 3a.

Reference： [1]Chemical Communications,2011,vol. 47,p. 7992 - 7994
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 11645 - 11650
[3]Tetrahedron,1995,vol. 51,p. 5341 - 5350
[4]Journal of Chemical Research,2006,p. 698 - 701
[5]Organic Letters,2012,vol. 14,p. 4466 - 4469
[6]European Journal of Medicinal Chemistry,2012,vol. 55,p. 125 - 136
[7]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5971 - 5975
[8]Organic Letters,2014,vol. 16,p. 484 - 487
[9]Journal of Organic Chemistry,2017,vol. 82,p. 13583 - 13593

7
[ 14187-32-7 ]
[ 54370-00-2 ]
[ 176911-77-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 741 - 746

8
[ 120-57-0 ]
[ 54370-00-2 ]
[ 473253-68-8 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 6973 - 6975
[2]Tetrahedron,2002,vol. 58,p. 5989 - 6001

9
[ 93-03-8 ]
[ 54370-00-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With lithium bromide monohydrate; [bis(acetoxy)iodo]benzene; In 2,2,2-trifluoroethanol; at 20℃; for 0.166667h;	General procedure: To a solution of alkoxybenzylalcohol 1 (0.2 mmol) in CF3CH2OH (1 mL) were added LiBr·H2O (0.2 mmol) and PhI(OAc)2 (0.2 mmol) atroom temperature. After completion of the reaction as indicated by TLC monitoring, saturated aq. Na2SO3 wasadded and the mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, driedover anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by silica gel columnchromatography to afford pure monobrominated compounds 2.

Reference： [1]Synlett,2018,vol. 29,p. 2275 - 2278
[2]Synthetic Communications,2004,vol. 34,p. 2143 - 2152
[3]Organic Letters,2006,vol. 8,p. 487 - 490
[4]Journal of Organic Chemistry,2008,vol. 73,p. 7509 - 7516

10
[ 54370-00-2 ]
Mo(CO)6 [ No CAS ]
[ 531-88-4 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 4635 - 4638

11
[ 620600-61-5 ]
[ 54370-00-2 ]
4-[2-(4-vinylphenoxy)ethyl]phenol [ No CAS ]
[ 137105-58-9 ]

Reference： [1]Journal of Chemical Research,2006,p. 698 - 701

12
[ 54370-00-2 ]
[ 14140-15-9 ]
[ 1008355-81-4 ]
[ 5392-10-9 ]

Reference： [1]Journal of Chemical Research,2006,p. 698 - 701

13
[ 54370-00-2 ]
[ 107-30-2 ]
[ 845302-11-6 ]

Yield	Reaction Conditions	Operation in experiment
63%		A solution of 0.53 g (1.43 mmol) of <strong>[54370-00-2]2-bromo-4,5-dimethoxybenzyl alcohol</strong> in 15 mL of anhydrous THF was cooled to 0C, and 0.04 g (1.58 mmol) of sodium hydride was added under argon. The mixture was stirred for 15 min, 0.12 g (1.43 mmol) of methoxymethyl chloride in 5 mL of anhydrous THF was added dropwise, and the mixture was stirred for 2 h at room temperature and for 2 h at 60C and left overnight at room temperature. The solvent was removed under reduced pressure, the viscous residue was dissolved in 30 mL of methylene chloride, and the solution was washed with water (3 7 mL). The product was isolated by column chro-matography using ethyl acetate-petroleum ether (1 : 4) as eluent. Yield 263 mg (63%), oily material. 1H NMR spectrum (200 MHz), δ, ppm: 3.40 s (3H, MeO), 3.83 s (3H, MeO), 3.85 s (3H, MeO), 4.57 s (2H, CH2), 4.71 s (2H, CH2), 6.96 s (1H, CH), 6.97 s (1H, CH). 13C NMR spectrum (50 MHz), δC, ppm: 55.5, 56.0, 56.2, 68.7, 96.0, 112.3, 113.2, 115.4, 129.2, 148.4, 149.0.

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3293 - 3301
[2]Russian Journal of Organic Chemistry,2016,vol. 52,p. 1481 - 1489
Zh. Org. Khim.,2016,vol. 52,p. 1489 - 1496,8
[3]European Journal of Organic Chemistry,2011,p. 1664 - 1681

14
[ 54370-00-2 ]
[ 937168-06-4 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3293 - 3301

15
[ 54370-00-2 ]
[ 937168-07-5 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3293 - 3301

16
[ 54370-00-2 ]
[ 937168-08-6 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3293 - 3301

17
[ 54370-00-2 ]
2,3,4,8,9-pentamethoxy-6H,11H-[2]benzopyrano[4,4-c][1]benzopyran-11-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3293 - 3301

18
[ 54370-00-2 ]
2,4,8,9-tetramethoxy-6H,11H-[2]benzopyrano[4,4-c][1]benzopyran-11-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3293 - 3301

19
[ 54370-00-2 ]
2,3,8,9-tetramethoxy-6H,11H-[2]benzopyrano[4,4-c][1]benzopyran-11-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3293 - 3301

20
[ 120-14-9 ]
[ 54370-00-2 ]

Reference： [1]Journal of Chemical Research,2006,p. 698 - 701
[2]Tetrahedron Letters,2001,vol. 42,p. 6973 - 6975
[3]Journal of Organic Chemistry,2000,vol. 65,p. 6398 - 6411
[4]Journal of the Chemical Society. Perkin transactions I,1993,p. 2599 - 2604
[5]Journal of Organic Chemistry,1990,vol. 55,p. 1471 - 1475
[6]Justus Liebigs Annalen der Chemie,1912,vol. 391,p. 44

21
[ 54370-00-2 ]
[ 878198-89-1 ]