Water → 2-(2-Bromophenoxy)cyclohexanone

HRID 342411Notes

Reaction equation

HRID 342411 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].Cl[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=[O:22].O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 132032-Chlorocyclohexanone

Product 1

HCID 539352372-(2-Bromophenoxy)cyclohexanoneYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-bromophenol (5 g), potassium carbonate (5.99 g) and 2-chlorocyclohexanone (4.22 g) in N,N-dimethylformamide was stirred at 60° C. for 4 hours. The reaction mixture was poured into cold water and the separated oil was extracted with diethyl ether. The extract was washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from n-hexane to give 2-(2-bromophenoxy)cyclohexanone (4.36 g).

Workup

  1. extractionthe separated oil was extracted with diethyl ether
  2. washThe extract was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-fdcd539dee8f43d48f694902bcd48d5f
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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