Benzene, 1-bromo-4-(trifluoromethyl)- → 4'-(Trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid

HRID 1784735Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[C:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([OH:14])=[O:13]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:18]2[CH:19]=[CH:20][C:15]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixed solution of ethylene glycol dimethyl ether (400 ml)-2M aqueous sodium carbonate solution (80 ml), 4-bromobenzotrifluoride (5.0 g), 4-carboxyphenylboronic acid (3.9 g) and tetrakistriphenylphosphinepalladium (2.5 g) were added and stirred at 100° C. for a day and night. Concentrating the reaction liquid under reduced pressure, the residue was extracted with 1N aqueous sodium hydroxide solution, and the aqueous layer was neutralized by gradual addition of conc. sulfuric acid. The precipitated solid was recovered by filtration, washed with water and diethyl ether and dried under reduced pressure to provide the title compound (4.2 g) as white solid.

Workup

concentrationConcentrating
customthe reaction liquid under reduced pressure
extractionthe residue was extracted with 1N aqueous sodium hydroxide solution
additionthe aqueous layer was neutralized by gradual addition of conc. sulfuric acid
filtrationThe precipitated solid was recovered by filtration
washwashed with water and diethyl ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-d8faafe0a96540189e61256568c08fed
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504412B2

Reaction notes

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