Dimethylformamide → HCID 86647429, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 751 mg (2.29 mmol) of O-(3,5-dibromophenylsulfonyl)-N-methylhydroxylamine, 159 mg (1.35 mmol) of Zn(CN)2 and 164 mg (0.142 mmol) of Pd(PPh3)4, 8 mL of DMF (degassed) was stirred at 80° C. After 70 min., 334 mg of Pd((PPh3)4, was added and after 35 min. 414 mg of Pd(PPh3)4 was added. After 1 h, EtOAc and 20 mL of 10% NH4OH (aq) was added, and the layers were separated. The organic layer was washed with 20 mL of 10% NH4OH (aq) and 20 mL of brine. The combined aqueous layer was extracted with EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography provided 194 mg of 3-bromo-5-(methylaminooxysulfonyl)benzonitrile as a yellow solid in 31% yield.

Provenance & Evidence