Bromine → 2-Bromo-6-phenylcyclohexanone

HRID 451398

Reaction equation

HRID 451398 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>[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 38%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-phenyl-cyclohexanone (10.0 g, 57 mmol) in CHCl3 (20 mL) at −10° C. a solution of bromine (9.6 g, 3.1 mL, 60 mmol) in CHCl3 (10 mL) was added and the reaction mixture was allowed to warm to 0° C. After for 2 hours the solvent was evaporated, methanol (30 mL) was added to the residue, cooled to 0° C., stirred for 30 minutes and the white solid was filtered off to give the title compound as a white solid (5.48 g, 38%).

Workup

  1. customAfter for 2 hours the solvent was evaporated
  2. additionmethanol (30 mL) was added to the residue
  3. temperaturecooled to 0° C.
  4. filtrationthe white solid was filtered off

Sources & evidence

ORD record
ord-f5f911b86ea04631a721f5a9248e2d3c
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Linked notes

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