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

HRID 2392631Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].B([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)(O)O.C(N(CC)CC)C>CN(C=O)C>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)=[C:3]([CH3:12])[CH:4]=1)=[O:7]

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-62fda537c60246ad842651f278eafe85
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05801170

Reaction notes

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