Water → 1-(4-hydroxyphenyl)-1H-indole

HRID 854494Notes

Reaction equation

HRID 854494 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-a1134267eb1949f0996304f9309d276e
Source dataset
uspto-grants-2007_08
Patent number
US07259182B2

Reaction notes

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