Sodium Carbonate → 1,1'-Biphenyl-4-carboxylic acid,4'-(trifluoromethyl)-,ethyl ester

HRID 1913764Notes

Reaction equation

HRID 1913764 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 22043Ethyl 4-bromobenzoateHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 547624251,1'-Biphenyl-4-carboxylic acid,4'-(trifluoromethyl)-,ethyl esterYield 70%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

7 g (30.56 mmol) of ethyl 4-bromobenzoate are dissolved in 60 ml of 1,2-dimethoxyethane and, under argon, 6.96 g (36.67 mmol) of 4-trifluoromethylphenylboronic acid, 271 mg of bis(triphenylphosphine)palladium(II) chloride and 40.7 ml of a 2 M aqueous sodium carbonate solution are added. The reaction mixture is then stirred under reflux for 12 hours. The mixture is then cooled, filtered through 1 g of Extrelute, washed with dichloromethane and concentrated. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/dichloromethane 2:1). 6.31 g (21.4 mmol, 70% yield) of a colourless solid are obtained.

Workup

  1. temperatureunder reflux for 12 hours
  2. temperatureThe mixture is then cooled
  3. filtrationfiltered through 1 g of Extrelute
  4. washwashed with dichloromethane
  5. concentrationconcentrated
  6. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/dichloromethane 2:1)

Sources & evidence

ORD record
ord-167cf49b04204ac9827812a0577a988e
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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