1-(4-Bromophenyl)propan-2-one → 1-(4-Bromophenyl)-2-methylpropan-2-ol

HRID 2223054Notes

Reaction equation

HRID 2223054 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[CH3:12][Mg]Br>C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([CH3:12])([OH:11])[CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7363321-(4-Bromophenyl)propan-2-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 3167851-(4-Bromophenyl)-2-methylpropan-2-olYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4-bromophenylacteone (6.85 g, 32 mmol) in diethyl-ether (100 ml) was cooled to 0° C. and treated with methylmagnesium bromide (23.5 ml of a 3M solution in diethyl-ether, 70 mmol). The reaction mixture was allowed to warm gradually to room temperature. After 2 hours the reaction was quenched by addition of saturated aqueous ammonium chloride (200 ml). The organic phase was separated and washed with saturated sodium chloride (100 ml), dried (sodium sulfate) and reduced in vacuo. Purification by flash column chromatography on silica gel eluting with pentane:dichloromethane (60:40 changing to 0:100, by volume) gave the title compound as a colourless oil (6.23 g, 84%).

Workup

  1. customAfter 2 hours the reaction was quenched by addition of saturated aqueous ammonium chloride (200 ml)
  2. customThe organic phase was separated
  3. washwashed with saturated sodium chloride (100 ml)
  4. dry with materialdried (sodium sulfate)
  5. customPurification by flash column chromatography on silica gel eluting with pentane:dichloromethane (60:40 changing to 0:100, by volume)

Sources & evidence

ORD record
ord-041b0b648ccd4818976879baba8772b3
Source dataset
uspto-grants-2008_05
Patent number
US07375100B2

Reaction notes

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