Diethyl Ether → 1-(4-Bromophenyl)-1-cyclohexylethanol

HRID 535318Notes

Reaction equation

HRID 535318 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.C[Mg+].[Br-].[CH2:19](OCC)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)([OH:9])[CH3:19])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24261645(4-Bromophenyl)(cyclohexyl)methanoneHCID 178418689HCID 178418689, compound

Product 1

HCID 438101371-(4-Bromophenyl)-1-cyclohexylethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-bromophenyl)(cyclohexyl)methanone (step 63.2) (3.1 g, 11.60 mmol) in THF (30 ml) was immersed in an ice-bath, followed by dropwise addition of MeMgBr (3M) in diethylether (7.74 ml, 23.21 mmol). The yellow reaction solution was stirred in the ice-bath for 1.5 hrs. The reaction mixture was quenched carefully with saturated aqueous NH4Cl solution and taken up in ethyl acetate. The organic phase was separated and washed with brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to obtain the title compound as yellow oil.

Workup

  1. customThe reaction mixture was quenched carefully with saturated aqueous NH4Cl solution
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb9ebaf0961e478695cf3fbd5eae330d
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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