Methanol → HCID 71295472, compound

Participants

Reaction Conditions

Reaction Steps

2-(5-chloro-2-methoxyphenyl)-4-fluoro-1H-indole (50 mg, 0.2 mmol) was dissolved in dichloromethane (1 mL), and then BBr3 (150 mg, 0.6 mmol) was added at −78° C. The mixture was stirred at −78° C. for 1 hour, and then stirred at 25° C. for 12 hours. MeOH (1 mL) and H2O (20 mL) were added to the solution. The mixture was extracted with ethyl acetate and washed with brine, dried over Na2SO4. After the combined organic layers were concentrated, the resulting residue was purified using prep-TLC (petroleum ether:EtOAc=5:1) to provide the product of 4-chloro-2-(4-fluoro-1H-indol-2-yl)phenol (10 mg, yield: 25%). 1H-NMR (CDCl3, 400 MHz) δ 9.54 (s, 1H), 7.65 (s, 1H), 7.06˜7.12 (m, 2H), 6.88 (s, 1H), 6.79˜6.81 (m, 1H), 6.70˜6.74 (m, 1H). MS (M+H)+: 262/263.

Provenance & Evidence