5-Bromosalicylic acid → 2-hydroxy-5-[4-(trifluoromethyl)phenyl]benzoic Acid

HRID 1984818Notes

Reaction equation

HRID 1984818 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1>>[OH:11][C:5]1[CH:4]=[CH:3][C:2]([C:17]2[CH:18]=[CH:19][C:14]([C:13]([F:24])([F:23])[F:12])=[CH:15][CH:16]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

3

Reactant 2

HCID 69725-Bromosalicylic acidHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 27827012-hydroxy-5-[4-(trifluoromethyl)phenyl]benzoic AcidYield 69.2%

Procedure

5-Bromo-2-hydroxy-benzoic acid (5 g, 23.04 mmol) was reacted with 4-trifluoromethyl phenyl boronic acid (6.56 g, 34.5 mmol) as desribed in general procedure D. The crude product was then was then purified by silica gel column chromatography (ethyl acetate:hexanes from 20:80 to 60:40) to afford 4.5 g of the 4-hydroxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid as a white solid.

Workup

  1. customThe crude product was then was then purified by silica gel column chromatography (ethyl acetate:hexanes from 20:80 to 60:40)

Sources & evidence

ORD record
ord-01a81137d9ea4b5198f536bbaee2eca5
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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