Dimethylformamide → 3'-Chloro-5-fluoro-6,4'-dimethoxy-biphenyl-3-carboxylic Acid Methyl Ester

HRID 1475779Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH3:12])=[C:6](Br)[CH:5]=1.[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)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.O>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:18]2[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:16]([Cl:15])[CH:17]=2)[C:7]([O:11][CH3:12])=[C:8]([F:10])[CH:9]=1)=[O:14]

Participants

Conditions

Temperature: 45 °C

Procedure

500 mg of 3-Bromo-5-fluoro-4-methoxy-benzoic acid methyl ester, 532 mg of 3-chloro-4-methoxyphenylboronic acid, 110 mg of tetrakis(triphenylphosphine) palladium(0), and 2.5 g Cs2CO3 were dissolved using 16.5 ml of DMF and 3.5 ml of water. The reaction mixture was stirred at 45° C. for 2 h and then poured into 75 ml of water. The reaction mixture was then extracted three times using 50 ml of EA each. The organic layer was washed twice using 25 ml of a half-saturated aqueous NaCl-solution, dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:3 yielded 500 mg of the title compound, viscous oil.

Workup

extractionThe reaction mixture was then extracted three times
washThe organic layer was washed twice
customdried
customevaporated

Sources & evidence

ORD record: ord-f64efd2a6fe44bcebb4527accda3124e
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018383B2

Reaction notes

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