Toluene → 4'-Methoxy-3'-methyl[1,1'-biphenyl]-4-carboxylic acid

HRID 1242801Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].I[C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C(O)CCC.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Methyl-4-methoxyphenylboronic acid (542 mg) was combined with 4-iodobenzoic acid (810 mg), cesium carbonate (5.32 g), toluene (16 mL), water (8 mL) and n-butanol (4 mL). The mixture was degassed under vacuum with argon purging after which, tetrakis-triphenylphosphine palladium (38 mg) was added. The reaction was heated to 80° C. for 20 hours after which, it was cooled to room temperature and diluted with ethyl acetate (16 mL). The layers were separated and the organics were concentrated to dryness. The residue was purified on silica gel (50% to 100% ethyl acetate/hexane over 40 minutes) giving 3′-methyl-4′-methoxy-4-biphenylcarboxylic acid (240 mg). Yield=30%

Workup

customThe mixture was degassed under vacuum with argon purging after which, tetrakis-triphenylphosphine palladium (38 mg)
additionwas added
temperaturewas cooled to room temperature
additiondiluted with ethyl acetate (16 mL)
customThe layers were separated
concentrationthe organics were concentrated to dryness
customThe residue was purified on silica gel (50% to 100% ethyl acetate/hexane over 40 minutes)

Sources & evidence

ORD record: ord-f9d29adc889840bbb96747d0034ffe83
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115741B2

Reaction notes

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