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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2177673Generated: October 30, 2026

Dimethylformamide → 6-(Benzenesulphonylmethyl)-3-cyano-2-methoxybenzoic acid

https://huagongshe.com/reaction/2177673

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant6-(Benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acidHCID 52913973—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
Solventtert-Butyl methyl etherHCID 15413—
Product6-(Benzenesulphonylmethyl)-3-cyano-2-methoxybenzoic acidHCID 52914291—

Reaction Conditions

Temperature180 °C

Reaction Steps

A mixture of 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acid (Example 7, 0.1 g), zinc cyanide (0.036 g) and tetrakis-(triphenylphosphine) palladium (0.015 g) in DMF was stirred and heated in the microwave at 180° C. for 10 minutes. After cooling, the mixture was diluted with t-butyl methyl ether, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by preparative HPLC (C18), eluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 35-98% to give 6-(benzenesulphonylmethyl)-3-cyano-2-methoxybenzoic acid (0.02 g) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09067905B2
Source datasetuspto-grants-2015_06
ORD IDord-2b88a298236244228abab729988c82af
Source noteuspto-grants-2015_06