Sodium hydride → 2-Bromo-N-(tert-butyloxycarbonyl)-N-(3-chloro-2-propen-1-yl) aniline

Participants

Reaction Conditions

Reaction Steps

A solution of 3.2 (350 mg, 1.29 mmol) in DMF (7 ml) was cooled to 0° C. and NaH (93 mg, 3.85 mmol) was added. The resulting mixture was stirred for 15 mins and 1,3 dichloropropene (358 μl, 3.85 mmol) was added. The mixture was allowed to warm to 25 ° C. and stirred for 15 h. The mixture was then concentrated. H2O (10 ml) was added to the residue and the solution was extracted with EtOAc (3×10 ml). The combined organic layers were dried with MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, EtOAc/Hex 1:9) to afford 3.3 (400 mg, 89%) as a pale yellow oil. FABMS (NBA/NaI) 346 (M+H+ expected 346).

Provenance & Evidence