4-Bromotryptophol

Synthesis

214915-73-8

202753-56-8

This embodiment demonstrates the procedure for the synthesis of 2-(4-bromo-1H-indol-3-yl)ethanol from ethyl 2-(4-bromo-3-indolyl)-2-oxoacetate. This was done as follows: lithium aluminum hydride (17.4 mg, 0.459 mmol) was added to a solution of tetrahydrofuran (THF, 1.4 mL) containing ethyl 2-(4-bromo-3-indolyl)-2-oxoacetate (20 mg, 0.0675 mmol), and the reaction mixture was subsequently refluxed for 2 hours. Upon completion of the reaction, the mixture was diluted with ethyl acetate and washed with water. The organic layer was dried with anhydrous magnesium sulfate (MgSO4) and filtered. Evaporation of the filtrate gave the crude product, which was purified by preparative thin layer chromatography (TLC) using a solvent mixture of hexane and ethyl acetate (1:1), resulting in the target product 2-(4-bromo-1H-indol-3-yl)ethanol (10 mg, 63% yield). The structure of the product was confirmed by 1H NMR and HRMS (ESI-MS): 1H NMR (CDCl3) δ 8.12 (1H, br s), 7.32 (1H, dd, J = 0.8 and 7.7 Hz), 7.28 (1H, dd, J = 0.8 and 7.7 Hz), 7.14 (1H, d, J = 2.5 Hz), 7.02 (1H, t, J = 7.8 Hz), 3.97 (2H, q, J = 6.1 Hz), 3.29 (2H, dt, J = 0.6 and 6.5 Hz), 1.46 (1H, t, J = 5.6 Hz); HRMS (ESI-MS m/z) calculated value of C10H11BrNO(M + H)+ 240.0024, measured value 240.0028.

References