Tetrahydrofuran → HCID 136377301, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (52 mL, 0.373 mol) is added to a stirred solution of 2-fluorobiphenyl-4-carboxylic acid (40 g, 0.185 mol) in tetrahydrofuran (800 mL). The reaction mixture is cooled to 5-15° C., iso-butyl chloroformate (36.5 mL, 0.28 mol) is added over a period of 20 minutes and stirred for 2 hrs at 15-20° C. A solution of N-hydroxy-4-hydroxymethylbenzamidine (36.9 g, 0.22 mol) in tetrahydrofuran (400 mL) is added to the reaction mixture and stirred for 2 hrs at 20-25° C. The reaction mixture is concentrated under reduced pressure, demineralized water (400 mL) is added to the residue and stirred for one hour at 5-10° C. The slurry is filtered, washed with demineralized water (400 mL) and dried under reduced pressure. The solid is stirred in 5% aqueous sodium bicarbonate solution (600 mL), filtered, washed with demineralized water and dried under reduced pressure. Finally the solid is washed with cyclohexane (600 mL) and dried under reduced pressure at 40-50° C. to give 2-fluorobiphenyl-4-carboxylic acid [hydroxyimino(4-hydroxy-methylphenyl)methyl]amide.

Provenance & Evidence