Boron tribromide → HCID 10802701, compound

HRID 1069637Notes

Reaction equation

HRID 1069637 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH2:19][C:20]([NH2:22])=[O:21])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(Br)(Br)Br>>[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH2:19][C:20]([NH2:22])=[O:21])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 10661460HCID 10661460, compound

Product 1

HCID 10802701HCID 10802701, compound

Procedure

4-Methoxy-1-(phenylmethyl)-1H-indole-3-acetamide (236 mg, 0.8 mmol) and 3.2 mL of BBr3 were reacted as described in Example 56, Part C, go give after chromatography en silica gel (eluted with 50% ethyl acetate/hexane) 78 mg (35% yield) of 4-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide.

Sources & evidence

ORD record
ord-b888d652d42f44f2b4963d3d9d2f612d
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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