Carbon tetrabromide → 3-Bromomethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one

HRID 1594892Notes

Reaction equation

HRID 1594892 reaction equation
O[CH2:2][C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH3:10])[C:4]1=[O:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39]>C(Cl)Cl>[Br:39][CH2:2][C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH3:10])[C:4]1=[O:11]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 217062823-Hydroxymethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one

Product 1

HCID 217061603-Bromomethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Hydroxymethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one (as described in Example 6, Step B) (0.60 g, 2.40 mmol), triphenylphosphine (0.94 g, 3.60 mmol), and carbon tetrabromide (1.19 g, 3.60 mmol) were dissolved in CH2Cl2 (15 mL), stirred under Ar for 16 h, then the solution was concentrated in vacuo and purified using SiO2 chromatography (0.5% MeOH/CH2Cl2) to give the title compound.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. custompurified

Sources & evidence

ORD record
ord-8dbbe6964df940b1af33c2fd86d1a749
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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