Boron tribromide → 1,3-Dimethyl-6-trifluoromethyl-1H-indol-5-ol

HRID 38436Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[N:8]([CH3:16])[CH:7]=[C:6]2[CH3:17].B(Br)(Br)Br>C(Cl)Cl>[CH3:16][N:8]1[C:9]2[C:5](=[CH:4][C:3]([OH:2])=[C:11]([C:12]([F:13])([F:14])[F:15])[CH:10]=2)[C:6]([CH3:17])=[CH:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

5-Methoxy-1,3-dimethyl-6-trifluoromethyl-1H-indole (725 mg, 3 mmol) in methylene chloride (15 ml) was cooled to zero degrees C., and BBr3 (14.9 ml of a 1 N solution in methylene chloride) was slowly added via syringe. The reaction mixture was stirred 15 minutes at zero degrees C., then allowed to warm to room temperature with stirring for one hour. The reaction mixture was quenched slowly with 75 mL 1 N NaOH. The mixture was acidified to pH 5 with 1 N HCl, extracted with methylene chloride, and the combined organic layers were washed with water, brine, and dried over magnesium sulfate. Solvent was removed under reduced pressure, and the residue was chromatographed (20% EtOAc/Hexanes) to give 235 mg (75%) 1,3-Dimethyl-6-trifluoromethyl-1H-indol-5-ol.

Workup

temperatureto warm to room temperature
stirringwith stirring for one hour
customThe reaction mixture was quenched slowly with 75 mL 1 N NaOH
extractionextracted with methylene chloride
washthe combined organic layers were washed with water, brine
dry with materialdried over magnesium sulfate
customSolvent was removed under reduced pressure
customthe residue was chromatographed (20% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-fdd8ba1c43e049eba9e99e8ec4e6d5a0
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524725B2

Reaction notes

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