Tert-Butyl nitrite → 1-Azido-2-chloro-4-cyclopropylbenzene

Participants

Reaction Conditions

Reaction Steps

2-Chloro-4-cyclopropylaniline (70 g, 418 mmol) was dissolved in Me-THF (2090 mL) and cooled to 0° C. in an ice bath. t-Butyl nitrite (59.8 mL, 501 mmol) was added slowly and TMSN3 (66.5 mL, 501 mmol) dropwise. The mixture was stirred at 0° C. for 30 min and gradually allowed to warm up to RT and stirred for 2 hrs. To the resulting mixture was added sat. NaHCO3 (aq) (250 mL) slowly under cooling, followed by water (250 mL). The mixture was transferred to a separating funnel and washed with water (1.5 L), dried over Na2SO4 and filtered to give the title compound which was used in the next step without further purification; HPLC Method D: Rt 5.63 mins;

Provenance & Evidence