Phosphorus tribromide → 1-(Bromomethyl)-2,3,4,5-tetramethoxy-6-methylbenzene
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH2:16]O.P(Br)(Br)[Br:19]>C1COCC1>[Br:19][CH2:16][C:4]1[C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[CH3:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,3,4,5-tetramethoxy-6-methylphenylmethanol (44.4 g) in THF (200 ml) was dropwise added phosphorus tribromide (29.8 g) with cooling with ice. After being stirred for 1 hr, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo to yield the entitled compound (54.4 g) as an oil.