Water → 1-(4-hydroxyphenyl)-1H-indole

HRID 2243157Notes

Reaction equation

HRID 2243157 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl.[Cl-].[Na+].O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 7757151-(4-methoxyphenyl)-1H-indole

Product 1

HCID 166556721-(4-hydroxyphenyl)-1H-indoleYield 26.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 2.90 g (13 mmol) 1-(4-methoxyphenyl)-1H-indole in 80 ml anhydrous DCM at −78° C. was added 2.27 ml (24 mmol) BBr3. The solution was allowed to gradually warm to room temperature overnight. The solution was poured into a slurry of ice and water. Brine was added and the product was extracted with ethyl acetate. The organic phase was dried over MgSO4 and concentrated. The crude product was chromatographed on SiO2 to afford 0.73 g 1-(4-hydroxyphenyl)-1H-indole as an oil.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on SiO2

Sources & evidence

ORD record
ord-22446ecb096948f2a60bcd2d0fd49a53
Source dataset
uspto-grants-2010_03
Patent number
US07674818B2

Reaction notes

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