Water → 4-Tert-butyl-3-fluoroaniline

Participants

Reaction Steps

NaBH4 (289 mg, 7.6 mmol) was added to a solution of 1-tert-butyl-2-fluoro-4-nitrobenzene (750 mg, 3.8 mmol) and NiCl2.6H2O (2.6 g, 11.4 mmol) in MeOH (15 mL) at −15° C. After addition, the mixture was stirred for 2 minutes and water was added to quench the reaction. The mixture was extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated in vacuo to afford 4-tert-butyl-3-fluoroaniline (470 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 7.08-7.02 (m, 1H), 6.42-6.34 (m, 2H), 1.32 (s, 9H). MS (ESI) m/z: 168.2 [M+H]+.

Provenance & Evidence