Chlorosuccinimide → (5Z)-N,1-dihydroxy-3,3-dimethyl-2,1-benzoxaborole-5-carboximidoyl chloride

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde oxime (1.38 g, 6.73 mmol) in DMF (15 mL) at rt was added NCS (1.07 g, 8.03 mmol). The reaction mixture was warmed to 45° C., stirred for 3 h and cooled to rt. The mixture was poured into ice-water (20 mL) and extracted with EA (20 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the desired product (1.7 g; 100% yield) as a white solid.

Provenance & Evidence