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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1475779Generated: October 30, 2026

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

https://huagongshe.com/reaction/1475779

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantCesium carbonateHCID 10796—
Reactant3-Chloro-4-methoxybenzeneboronic acidHCID 3247522—
ReactantMethyl 3-bromo-5-fluoro-4-methoxybenzoateHCID 67076673—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
SolventWaterHCID 962—
Product3'-Chloro-5-fluoro-6,4'-dimethoxy-biphenyl-3-carboxylic Acid Methyl EsterHCID 6717130681%

Reaction Conditions

Temperature45 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09018383B2
Source datasetuspto-grants-2015_04
ORD IDord-f64efd2a6fe44bcebb4527accda3124e
Source noteuspto-grants-2015_04