Sodium Carbonate → 3-Chloro-4'-fluoro[1,1'-biphenyl]-4-carboxylic acid

HRID 1867537Notes

Reaction equation

HRID 1867537 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:11][C:4]1[CH:3]=[C:2]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1088294-Bromo-2-chlorobenzoic acidHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 463144703-Chloro-4'-fluoro[1,1'-biphenyl]-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Under an inert atmosphere, 5 g (21.2 mmol) of 4-bromo-2-chlorobenzoic acid, 2.96 g (23.3 mmol) of 4-fluorophenylboronic acid and 31.8 ml (63.6 mmol) of aqueous sodium carbonate solution (2M) in suspension in 40 ml of toluene are introduced. Subsequently 0.80 g (0.70 mmol) of palladium tetrakis(triphenylphosphine) is added. The reaction mixture is subsequently refluxed overnight.

Sources & evidence

ORD record
ord-0cb48b9257824cb096b9710ec06aae39
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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