1,1-Dibromoethane → 5-Nitro-2,3-dihydro-1,4-benzodioxine

Participants

Reaction Steps

3-Nitro-1,2-benzenediol (5 g; 32.26 mmol), dibromoethane (12.13 ml; 64.52 mmol), tetra(n-butyl)ammonium bromide (1.1 g; 32.26 mmol) and K2CO3 (13.35 g; 96.78 mmol) were stirred at reflux in toluene overnight. The reaction was then poured onto water (150 ml) and twice extracted with diethyl ether (2×150 ml). The combined organics were washed with water (100 ml) and brine (100 ml) then dried with MgSO4 and the solvents removed to afford the desired product (5.4 g; 93%).

Provenance & Evidence