6-nitro-4-(trifluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol → HCID 68281360, compound

Participants

Reaction Steps

To a solution of 6-nitro-4-(trifluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol (CXXXI) (0.95 g, 3.83 mmol) in MeOH/2M HCl mixture (1:1) (129 mL) was added Zn (dust) (2.5 g, 38.31 nmol). The reaction mixture was stirred at room temperature for 3 hours before it was slowly neutralized by a solution of saturated aq. NaHCO3/EtOAc (1:1, 100 mL/100 mL). Then the reaction mixture was filtered through Celite and washed with EtOAc. The organic layer was washed with 5% NaHCO3, brine, dried over anhydrous MgSO4, filtered and evaporated to dryness to yield 6-amino-4-(trifluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol (CXXXII) as a slightly brown crystalline solid (700 mg, 3.22 mmol, 84% yield). ESIMS found for C8H7BF3NO2 m/z 216.4 (M−H).

Provenance & Evidence