Cyclohexyl bromide → 1-Cyclohexyl-2-methylbenzene

HRID 476328

Reaction equation

HRID 476328 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Mg]Br.N1C=CN=CC=1>C1COCC1>[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7960Cyclohexyl bromideHCID 9261PyrazineHCID 178424303HCID 178424303, compound2×

Product 1

HCID 5999381-Cyclohexyl-2-methylbenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Bromocyclohexane (81.7 mg, 0.5 mmol) and a THF solution (0.94 mL, 0.80 M, 0.75 mmol) of 2-methylphenylmagnesium bromide were used as starting materials, and reacted as in Entry 1. Conditions: The THF solution of 2-methylphenylmagnesium bromide was added dropwise at 40° C. over 20 minutes. 1H-NMR analysis was conducted using pyrazine (13.2 mg, 0.16 mmol) as an internal standard (yield 99%).

Workup

  1. custommaterials, and reacted as in Entry 1

Sources & evidence

ORD record
ord-1843bf8c1ed5453c846dfb4e2ca277c9
Source dataset
uspto-grants-2014_01
Patent number
US08637710B2

Linked notes

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