Benzyl Bromide → 1H-Indol-5-ol, 1-(phenylmethyl)-
Reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:7]=[CH:6]2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
5-Methoxy-1H-indole (5.6 g, 21.5 mmol) was reacted with 1.0 g (25 mmol) of 60% sodium hydride and then 3.0 mL (25 mmol) of benzyl bromide by the method described in Example 12, Part D to give crude 5-methoxy-1-(phenylmethyl)-1H-indole. This material was dissolved in 250 mL of methylene chloride, cooled to -5° C., 50 mL of 1M BBr3/CH2Cl2 added, the cooling bath removed and the mixture stirred for 1.75 hours: Ice water was added and the mixture stirred. The organic layer was separated, washed with saturated NaCl, dried (Na2SO4), and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% ether/hexane→ether to give 870 mg (19% overall yield) of crude 5-hydroxy-1-(phenylmethyl)-1H-indole.
Workup
- customto give crude 5-methoxy-1-(phenylmethyl)-1H-indole
- customthe cooling bath removed
- additionIce water was added
- stirringthe mixture stirred
- customThe organic layer was separated
- washwashed with saturated NaCl
- dry with materialdried (Na2SO4)
- concentrationconcentrated at reduced pressure
- customThe residue was chromatographed on silica gel
- washeluted with 20% ether/hexane
Sources & evidence
- ORD record
- ord-43e66668e4564d37a952466ed79f18fb
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05919943
Reaction notes
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