Bromine → 2-Bromo-6-phenylcyclohexanone

HRID 273761

Reaction equation

HRID 273761 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:14]Br>C(Cl)(Cl)(Cl)Cl>[Br:14][CH:9]1[CH2:10][CH2:11][CH2:12][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]1=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 955922-Phenylcyclohexanone

Product 1

HCID 127791292-Bromo-6-phenylcyclohexanoneYield 43.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 15 g (86 mmole) of 2-phenylcyclohexanone in 60 mL of carbon tetrachloride at -5° C. was treated via rapid dropwise addition with a solution of 14.4 g (90 mmole) of bromine in 70 mL of carbon tetrachloride so as to maintain the reaction temperature below 5° C. The color disappeared rapidly. The mixture was concentrated in vacuo to a brown solid and the solid triturated with methanol. The resulting white solid was collected by filtration to provide 9.55 g of product. After cooling the mother liquor at -25° C., an additional 5.2 g of solid was obtained, for a total yield of 68%, a portion of which was carried on directly in Step B below.

Workup

  1. temperatureto maintain the reaction temperature below 5° C
  2. concentrationThe mixture was concentrated in vacuo to a brown solid
  3. customthe solid triturated with methanol
  4. filtrationThe resulting white solid was collected by filtration

Sources & evidence

ORD record
ord-f5aea3c16def4f2c9c9c9c482b76b49d
Source dataset
uspto-grants-1995_02
Patent number
US05387595

Linked notes

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