Sodium Carbonate → Methyl 4'-fluoro-3-isopropoxybiphenyl-4-carboxylate

HRID 2272467Notes

Reaction equation

HRID 2272467 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH:13]([CH3:15])[CH3:14])[CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH:13]([CH3:15])[CH3:14])[CH:3]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 90422834Methyl 4-iodo-2-isopropoxybenzoate

Product 1

HCID 117992325Methyl 4'-fluoro-3-isopropoxybiphenyl-4-carboxylateYield 97.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 4-iodo-2-isopropoxybenzoate (7.50 g), (4-fluorophenyl)boronic acid (6.56 g), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (1.44 g), a 2 M aqueous sodium carbonate solution (35.1 mL), tris(dibenzylideneacetone)dipalladium(0) (1.50 g), and toluene (50 mL) was stirred at 100 C for 2 hours in an argon atmosphere. The reaction mixture was allowed to cool to room temperature. Then, the organic layer was separated and passed through a short silica gel (NH) column, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (6.61 g).

Workup

  1. customThen, the organic layer was separated
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cf7cc5adc1a54d00bab1d92e7527ba99
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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