Diethyl Ether → (4-Bromophenyl)(cyclohexyl)methanol

HRID 535320Notes

Reaction equation

HRID 535320 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]1([Mg]Cl)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(OCC)C>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[OH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 707414-BromobenzaldehydeHCID 178478990HCID 178478990, compound

Product 1

HCID 11402947(4-Bromophenyl)(cyclohexyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromobenzaldehyde (4.5 g, 24.32 mmol) in THF (40 ml) was immersed in an ice/methanol bath, followed by the dropwise addition of cyclohexylmagnesium chloride (2M) in diethylether (18.24 ml, 36.5 mmol) at −1° C. to +2° C. The reaction was allowed to warm up to room temperature and the reaction was stopped after 1 hr. The reaction mixture was quenched with saturated aqueous NH4Cl solution before dilution with 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 crude product which was purified by flash chromatography (normal phase, n-heptane (isom. mixture)/ethyl acetate 4:1) to obtain the title compound as yellow oil.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NH4Cl solution before dilution with ethyl acetate
  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
  7. customto obtain the crude product which
  8. customwas purified by flash chromatography (normal phase, n-heptane (isom. mixture)/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-b095977865ad41a0b19e3873db704219
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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