Triethylamine → HCID 59656668, compound

Participants

Reaction Steps

To a stirred solution of the above benzoic acid intermediate (3 g, 14.34 mmol) and triethylamine (4.5 g, 44.47 mmol) in dry THF (30 mL) at −10° C. was added ethyl chloroformate (2.5 g, 23.04 mmol). The reaction was stirred for 1 h and monitored by TLC (20% EtOAc in CH2Cl2). A solution of NaN3 (2.3 g, 35.34 mmol) in water (15 mL) was added dropwise to the mixture and stirred for 2 h. The mixture was diluted with water (40 mL) and extracted with toluene (3×20 mL). The extract was washed with brine and dried over Na2SO4. The solvent was removed in vacuo to give 3-cyano-4-ethoxy-2-fluoro-benzoyl azide (2.5 g, 39.2%).

Provenance & Evidence