2,3-Difluorophenol → 2-(4-Chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-ethanone

HRID 14457

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](Cl)=[O:14])=[CH:8][CH:7]=1.[F:16][C:17]1[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=1[OH:24]>ClCCCl.O>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([C:19]2[CH:20]=[CH:21][C:22]([F:23])=[C:17]([F:16])[C:18]=2[OH:24])=[O:14])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of aluminium chloride (7.66 g, 57.4 mmol, 1.5 eq.) and (4-chlorophenyl)acetyl chloride (8.7 g, 46 mmol, 1.2 eq.) in 1,2-dichloroethane (75 ml) is stirred at 0° C. for 30 min. A solution of 2,3-difluorophenol (5 g, 38.4 mmol) in 1,2-dichloroethane (25 ml) is added to the reaction mixture, which is heated in an oil bath at 90° C. overnight. The reaction mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic phase is dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to afford a brown solid. This is triturated with hexane/ethyl acetate (9:1), filtered and dried to afford the title compound as a pale brown fine solid which is 87% pure by HPLC analysis.

Workup

temperatureis heated in an oil bath at 90° C. overnight
temperatureThe reaction mixture is cooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe organic phase is dried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated to dryness in vacuo
customto afford a brown solid
customThis is triturated with hexane/ethyl acetate (9:1)
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-9bbf5b40766140ed82fefb6b7021adb9
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732435B2

Linked notes

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