Water → Methyl 6-methoxy-[1,1'-biphenyl]-3-carboxylate

HRID 1893152Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].O.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CO>[CH3:13][O:12][C:11]1[C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of methyl 3-bromo-4-methoxybenzoate (13 g, 53 mmol) in toluene (500 mL), methanol (65 mL), and water (106 mL) was added phenyl boronic acid (7.8 g, 63.6 mmol) and potassium carbonate (14.6 g, 106 mmol) and bubbled with argon for 6 min. Tetrakis(triphenylphosphine)palladium(0) (370 mg) was added and bubbled with argon for another 2 min. The reaction mixture was then heated to 95° C. for 20 h with stirring. After cooling to RT, the two phases were separated and the aqueous layer was extracted with ether, dried with magnesium sulfate, and concentrated. Purification by MPLC (5% ethyl acetate in hexanes) gave 12.2 g of the desired product as an off white solid.

Workup

custombubbled with argon for 6 min
additionTetrakis(triphenylphosphine)palladium(0) (370 mg) was added
custombubbled with argon for another 2 min
temperatureAfter cooling to RT
customthe two phases were separated
extractionthe aqueous layer was extracted with ether
dry with materialdried with magnesium sulfate
concentrationconcentrated
customPurification by MPLC (5% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-a0abcecc903e432689d0d74e96949149
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513220B2

Reaction notes

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