The general procedure for the synthesis of 7-bromo-1,2,3,4-tetrahydroisoquinoline from N-trifluoroacetyl-7-bromo-1,2,3,4-tetrahydroisoquinoline was as follows: 1-(7-bromo-3,4-dihydro-1H-isoquinolin-2-yl)-2,2,2-trifluoroacetophenone (14.3 g, 46.4 mmol) was added to a mixture of methanol (50 mL) and saturated sodium carbonate solution ( 50 mL) to a mixture of methanol (50 mL) and saturated sodium carbonate solution (50 mL). The reaction mixture was stirred at 60 °C for 1 hour. After completion of the reaction, the mixture was concentrated and the residue was extracted with ethyl acetate. The organic layers were combined, washed sequentially with water and brine, and then dried over anhydrous sodium sulfate. After evaporation of the solvent, the crude product was purified by column chromatography to afford the light yellow solid product 7-bromo-1,2,3,4-tetrahydroisoquinoline (8.4 g, 85% yield). Mass spectrometry analysis showed m/z 213.8 (M + 1).
