Cyclohexyl bromide → 1-Cyclohexyl-4-methoxybenzene

HRID 476329

Reaction equation

HRID 476329 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1.N1C=CN=CC=1>C1COCC1>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7960Cyclohexyl bromideHCID 9261PyrazineHCID 178491912HCID 178491912, compound2×

Product 1

HCID 2215261-Cyclohexyl-4-methoxybenzeneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Bromocyclohexane (81.8 mg, 0.5 mmol) and a THF solution (0.85 mL, 0.88 M, 0.75 mmol) of 4-methoxyphenylmagnesium bromide were used as starting materials, and reacted as in Entry 1. Conditions: The THF solution of 4-methoxyphenylmagnesium bromide was added dropwise at 25° C. over 20 minutes. 1H-NMR analysis was conducted using pyrazine (19.0 mg, 0.24 mmol) as an internal standard (yield 96%).

Workup

  1. custommaterials, and reacted as in Entry 1

Sources & evidence

ORD record
ord-70edcfce12f74e29852fa6f91783a422
Source dataset
uspto-grants-2014_01
Patent number
US08637710B2

Linked notes

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