N,N-Dimethylaniline → (Z)-methyl 3-bromo-6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-2-hydroxybenzoate

Participants

Reaction Steps

Aluminium chloride (0.303 g) was added to a stirred solution of (Z)-methyl 3-bromo-6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-2-methoxybenzoate (Intermediate 161, 0.528 g) and N,N-dimethylaniline (0.915 g) in DCM (20 ml). The resultant mixture was stirred for 3 hours then a mixture of ice, water and DCM were added. The organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-6% to give (Z)-methyl 3-bromo-6-((2-(3-(diethylamino)prop-1-enyl)-4-fluorobenzenesulfonyl)methyl)-2-hydroxybenzoate (0.514 g) as a pale purple oil.

Provenance & Evidence