Bromine → 6-Bromo-2-methyl-2-phenyl-cyclohexanone

HRID 2076027Notes

Reaction equation

HRID 2076027 reaction equation
[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][CH:4]1[C:3](=[O:8])[C:2]([CH3:1])([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 24408BromineHCID 3499432-Methyl-2-phenylcyclohexanone

Product 1

HCID 581100436-Bromo-2-methyl-2-phenyl-cyclohexanoneYield 101.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 2-methyl-2-phenyl-cyclohexanone (0.94 g, 5.0 mmol) in chloroform (12 mL) at −5° C. was treated via rapid dropwise addition with a solution of bromine (0.26 mL, 5.1 mmol) in chloroform (6 mL) so as the reaction temperature maintaining below 5° C. The solution was kept at 0° C. for 2 h when the red color had disappeared. The mixture was concentrated under reduced pressure to give the crude title compound (1.35 g, 100%) as a brown oil which was used directly in the next step. MS ISP (m/e): 267.3 [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=7.22-7.42 (m, 3H), 7.13 (d, 2H), 4.70 (dd, 1H), 2.75 (m, 1H), 2.52 (m, 1H), 1.7-2.4 (m, 4H), 1.36 (s, 3H).

Workup

  1. temperaturemaintaining below 5° C
  2. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-89ae59426a7940c5afffe5e42ed97672
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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