N-bromobutanimide → 4-Bromo-7-methoxy-2-methoxymethylbenzofuran
Reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH2:12][O:13][CH3:14])=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[Br:15]N1C(=O)CCC1=O>C(#N)C>[Br:15][C:6]1[C:7]2[CH:8]=[C:9]([CH2:12][O:13][CH3:14])[O:10][C:11]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 7-methoxy-2-methoxymethylbenzofuran (13.32 g) in acetonitrile (500 ml) was stirred at room temperature. N-bromosuccinimide (11.04 g) was added and stirring continued for 2 days after which the solvent was removed in vacuo. The resulting oil was partitioned between ethyl acetate (100 ml) and sodium metasulfite solution (50 ml), the organic extract washed with more sodium metasulfite solution (2×50 ml), followed by brine (50 ml). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo to afford the title compound as a yellow oil (18.61 g).