Water → HCID 19092865, compound

HRID 487661Notes

Reaction equation

HRID 487661 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:16](=[CH:17][C:18]([CH3:23])=[C:19]([CH3:22])[CH:20]=3)[NH:15][C:14]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:9][CH:8]=1.O>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:21]3[C:16](=[CH:17][C:18]([CH3:23])=[C:19]([CH3:22])[CH:20]=3)[NH:15][C:14]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 19092867HCID 19092867, compound

Product 1

HCID 19092865HCID 19092865, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (BBr3) (0.18 ml) in dichloromethane (0.36 ml) was dropwise added to a solution of methyl 3-(4-methoxyphenyl)-5,6-dimethylindole-2-carboxylate (0.3 g) in dichloromethane (10 ml) at 0° C. The reaction mixture was stirred for 2 hours at the same temperature, poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The precipitated crystals were collected by filtration and recrystallized from acetone to give methyl 3-(4-hydroxyphenyl)-5,6-dimethylindole-2-carboxylate (0.127 g, 44%) as colorless needles.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe precipitated crystals were collected by filtration
  6. customrecrystallized from acetone

Sources & evidence

ORD record
ord-d4f1e8b005a74ea09fb1b6fbd59b4d74
Source dataset
uspto-grants-1994_03
Patent number
US05296499

Reaction notes

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