Bromine → 1-(4'-Chlorophenyl)-2-bromo-4,4-dimethylpentan-3-one

HRID 1389003Notes

Reaction equation

HRID 1389003 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH2:7][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[Br:16]Br>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]([Br:16])[C:8](=[O:13])[C:9]([CH3:10])([CH3:11])[CH3:12])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 946171-(4-Chlorophenyl)-4,4-dimethyl-3-pentanone

Product 1

HCID 129406931-(4'-Chlorophenyl)-2-bromo-4,4-dimethylpentan-3-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

4-Chlorobenzylpinacolone (11.2 g) in carbon tetrachloride (80 ml) was cooled to about 5° and bromine (8 g) in carbon tetrachloride (20 ml) added dropwise at that temperature over 2 hours. Care was taken to keep free bromine to a minimum in the reaction mixture in order to avoid byproduct formation. The solution was washed with saturated aqueous sodium bicarbonate and with water, dried (magnesium sulphate), and concentrated in vacuo to afford, as a white crystalline solid, crude 1-(4'-chlorophenyl)-2-bromo-4,4-dimethylpentan-3-one, m.p. 48°-50°.

Workup

  1. washThe solution was washed with saturated aqueous sodium bicarbonate and with water
  2. dry with materialdried (magnesium sulphate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eebc9d3ef481476ba8a7157196f1c9b7
Source dataset
uspto-grants-1981_01
Patent number
US04243405

Reaction notes

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