Dimethylformamide → 4'-(Methoxycarbonyl)-2'-methyl-[1,1'-biphenyl]-4-carboxylic acid

HRID 1741052Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10](C)=NN=2)=[CH:4][C:3]=1[CH3:14].B([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)(O)O.C(N(CC)CC)C.CN(C=[O:38])C>[Pd].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>[CH3:10][O:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)=[C:3]([CH3:14])[CH:4]=1)=[O:38]

Participants

Conditions

Temperature: 100 °C

Procedure

A stirred solution of methyl 4-bromo-3-methylbenzoate (EP 0533268 A1) (1.0 g, 0.0044 mole) in dry DMF (10 ml) under argon was treated with 4-boronobenzoic acid (0.73 g, 0.0044 mole) and tetrakis (triphenylphosphine) palladium(0) (80 mg), followed by triethylamine (1.8 ml, 0.016 mole), the mixture was heated at 100° C. for 18 hours, then concentrated in vacuo. The residue was treated with ethyl acetate and extracted with 10% NaHCO3 solution. The basic extract was acidified with dil. HCl and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound as a white solid (0.46 g, 39%).

Workup

concentrationconcentrated in vacuo
additionThe residue was treated with ethyl acetate
extractionextracted with 10% NaHCO3 solution
extractionThe basic extract
extractionextracted with ethyl acetate
dry with materialThe extract was dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f2ad52dbd9034e57b7b54e474b49f25f
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972951

Reaction notes

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