Sodium Carbonate → 5-Bromo-6-(4-fluorophenyl)-1,3-benzodioxole

Participants

Reaction Steps

Under nitrogen, 1.1 g of Pd(PPh3)4 was added to a stirred solution of 10.4 g (37.2 mmol) of 5,6-dibromo-1,3-benzodioxole and 2.6 g (18.6 mmol) of 4-fluorophenylboronic acid in 100 mL of toluene, 60 mL of ethanol, and 40 mL of 2M Na2CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, and dried over Na2SO4. Purification by silica gel chromatography (Waters Prep-500A) with hexane as the eluent gave 3.9 g (71%) of 5-bromo-6-(4-fluorophenyl)-1,3-benzodioxole as a colorless solid: mp 86.0-87.5° C.; NMR (CDCl3) δ 6.02 (s, 2H), 6.77 (s, 1H), 7.04-7.13 (m, 3H), 7.28-7.35 (m, 2H)

Provenance & Evidence