Water → HCID 14501061, compound

Participants

Reaction Steps

To a solution of N-bromosuccinimide (10.7 g, 0.06 mol) in dry DMF (70 ml) was added dropwise and with stirring a solution of 5-phenylmethoxy-1,3-benzodioxole (13.68, 0.06 mol) in dry DMF (80 ml). The resulting solution was stirred for 24 h at room temperature, poured into 300 ml of H2O and extracted with chloroform (3×70 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was recrystallized from absolute EtOH affording 17.4 g (94.5%) of 6-bromo-5-phenylmethoxy)-1,3-benzodioxole as white crystals mp 61.5°-62° C.; NMR (CDCl3, 90 MHz) δ 5.04 (S, 2H, CH2Ph), 5.91 (S, 2H, OCH2O), 6.56 (S, 1H, ArH), 6.99 (S, 1H, ArH), 7.14-7.63 (m, 5H, CH2Ph). Anal. calcd. for C14H11BrO3 : C, 54.75; H, 3.61; Br, 26.01. Found: C, 54.81; H, 3.64; Br, 25.68.

Provenance & Evidence