Water → 6-Bromoindole

Participants

Reaction Conditions

Reaction Steps

To a mixture solution of 4-bromo-2-nitrotoluene (2.00 g, 9.26 mmol) and dimethylformamide-dimethylacetal (3.68 mL, 27.8 mmol) in DMF (20 mL), pyrrolidine (1.16 mL, 13.9 mmol) was added at room temperature. After stirring at 110° C. for an hour, the mixture was cooled to room temperature and then water was added. After extracting 3 times with ether, the collected organic layer was dried with anhydrous magnesium sulfate and the concentrated. The resulting residue was subjected to the next reaction without purification. After adding 80% acetic acid aqueous solution (60 mL), the mixture was heated to 85° C. While adding zinc powder (5.27 g, 80.6 mmol) in small amounts, the mixture was stirred at 85° C. for 2 hours. After cooling to room temperature and filtering, followed by addition of water, the filtrate was extracted with ethyl acetate. The collected organic layer was washed with brine and concentrated by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (silica gel, EA:Hx=1:20). The target compound (710 mg) was obtained as violet solid.

Provenance & Evidence