Phenacyl bromide → 2-(2-Bromophenoxy)-1-phenylethan-1-one

HRID 322027Notes

Reaction equation

HRID 322027 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 72442-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 30163542-(2-Bromophenoxy)-1-phenylethan-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-bromophenol (8.71 g; 50.3 mmol) and bromoacetophenone (10.1 g; 50.5 mmol) in 50 ml acetone was added K2CO3 (7.02 g; 50.8 mmol). The mixture was heated to reflux for 10 h, cooled to r.t., filtered, diluted with EtOAc (100 ml), washed with HCl (1.0 M, 2×100 ml) and brine, dried over MgSO4 and concentrated. The residual solid was recrystallized from EtOAc:hexane to afford the desired material.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 10 h
  3. filtrationfiltered
  4. additiondiluted with EtOAc (100 ml)
  5. washwashed with HCl (1.0 M, 2×100 ml) and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residual solid was recrystallized from EtOAc

Sources & evidence

ORD record
ord-e8ea565d4667442bad8a8029ce85b129
Source dataset
uspto-grants-2001_04
Patent number
US06211197B1

Reaction notes

Loading…