Dimethylformamide → tert-butyl N-(4-chloro-3-(hydroxymethyl)phenyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of 5-amino-2-chlorobenzoic acid (9.0 g; 33 mmol) in THF:DMF (200 mL; 1:1) was added TEA (4.0 g; 40 mmol), followed by isobutyl chloroformate (5.4 g; 40 mmol; added dropwise). The mixture was then stirred for another 30 minutes, the white precipitate formed was removed by filtration, the filtrate was cooled to −15° C., and NaBH4 (3.8 g; 100 mmol) and water (20 mL) were added. After 15 minutes, water (200 mL) was added and the solution was stirred at room temperature for 1 hour. After evaporation, the residue was dissolved in MeOH. Filtration and concentration gave the crude product which was purified by flash chromatography (Si-gel, CH2Cl2:MeOH (9:1)) resulting in 7.4 g (87%) of the sub-title compound.

Provenance & Evidence