Water → 2-Bromo-3-methylcyclohexanone

HRID 12055

Reaction equation

HRID 12055 reaction equation
[Br:1]N1C(=O)CCC1=O.C([O-])(=O)C.[Na+].C[Si](C)(C)[O:16][C:17]1[CH2:22][CH2:21][CH2:20][CH:19]([CH3:23])[CH:18]=1.O>C1COCC1.O.C(OCC)(=O)C>[Br:1][CH:18]1[CH:19]([CH3:23])[CH2:20][CH2:21][CH2:22][C:17]1=[O:16]

Participants

7

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 517045Sodium AcetateHCID 597981Trimethyl-(3-methyl-cyclohex-1-enyloxy)-silane

Product 1

HCID 215419562-Bromo-3-methylcyclohexanone

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of N-bromosuccinimide (0.48 mmol) and sodium acetate (0.04 mmol) in THF/water (1:1, 5.2 ml) is cooled to 0° C. and trimethyl-(3-methyl-cyclohex-1-enyloxy)-silane (0.4 mmol, 80% pure) is added dropwise. The reaction mixture is heated to room temperature and stirring is continued overnight. After addition of water extraction is carried out with ethyl acetate. The title compound is obtained from the combined organic phases after drying over sodium sulphate and evaporating-off of the solvent in a vacuum (JOC 1997, 62, 19, 6692-6696).

Sources & evidence

ORD record
ord-9141ed1670cb49bcba55b96621509c0b
Source dataset
uspto-grants-2010_06
Patent number
US07727979B2

Linked notes

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