Ethanol → Ethyl acetate methanol ammonia

Participants

Reaction Conditions

Reaction Steps

Compound 15 was prepared using the procedures of Steps 1-2 of Example 5, substituting 5-bromo-2-fluoronitrobenzene for 2,5-dichloronitrobenzene in Step 1. Step 3: A suspension of 15 (6.2 g, 10 mmol) in EtOH (20 ml) was treated with SnCl2 (9.5 g, 50 mmol), heated to reflux for 3 h, and then stirred overnight at 20° C. The reaction mixture was poured on saturated aqueous NaHCO3, extracted with CH2Cl2, dried over Na2SO4, and concentrated. Chromatography (5% 1 N NH3-MeOH/EtOAc) provided the title compound (5.2 g, 52%) as a yellow solid. MS: (M+1) 487.

Provenance & Evidence