Water → 2-methyl-1H-indol-5-ol

HRID 45055

Reaction equation

HRID 45055 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[CH:6]2.B(Br)(Br)Br.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:12][C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([OH:2])=[CH:11][CH:10]=2

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 706425-Methoxy-2-methylindoleHCID 516892Sodium Bicarbonate

Product 1

HCID 833362-methyl-1H-indol-5-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a precooled (0° C.) solution of 5-methoxy-2-methyl-1H-indole (5.0 g, 31.0 mmol) in 100 mL DCM is added BBr3 (1 M solution, 46.5 mL) under a dry nitrogen atmosphere. The solution is then allowed to slowly warm to room temperature over a 2 h period. The solution is then poured into water, neutralized to pH 7 with sat aq sodium bicarbonate solution and extracted with EtOAc. The extract is washed by brine, dried over sodium sulfate, and concentrated to give 2-methyl-1H-indol-5-ol. MS (ESI) m/z 148.2 (M+1).

Workup

  1. extractionextracted with EtOAc
  2. washThe extract is washed by brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b30c5c351fed413b95d91178fdf4d9d0
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Linked notes

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