Aluminum(III) Chloride → 6-Bromoisoquinoline
Reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:29]=[CH:28][C:9]([CH2:10][N:11]([CH2:22][CH:23](OC)OC)S(C2C=CC(C)=CC=2)(=O)=O)=[CH:8][CH:7]=1>ClCCl>[Br:5][C:6]1[CH:29]=[C:28]2[C:9](=[CH:8][CH:7]=1)[CH:10]=[N:11][CH:22]=[CH:23]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mechanically stirred suspension of 95.2 g (699.5 mmol) of AlCl3 in 400 ml of dichloromethane a solution of 59.9 g (139.8 mmol) N-(4-bromo-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzenesulfonamide (2) in 400 ml of dichloromethane was added and the reaction was stirred at room temperature for 4 h. After standing overnight, the reaction mixture was poured onto ice, the organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined dichloromethane solutions were washed with 1 N NaOH (2×) and saturated sodium hydrogen carbonate-solution (2×). After drying with magnesium sulfate and evaporation of the solvent, the crude product was purified by silica gel chromatography (heptane/ethyl acetate 1:1) to yield 17.5 g of the title compound. Rt=0.68 min (Method C). Detected mass: 208.1/210.1 (M+H+).