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

HRID 81851Notes

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-c4d3ee0ea7f3459f8f96f20170d4cc8b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846705B2

Reaction notes

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