p-Bromoacetophenone → 2-(4-Bromophenyl)propan-2-ol

HRID 1691427Notes

Reaction equation

HRID 1691427 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][Mg]Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])([CH3:11])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7466p-BromoacetophenoneHCID 178418332HCID 178418332, compound

Product 1

HCID 126819202-(4-Bromophenyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-(4-bromophenyl)ethanone (8 g, 40.2 mmol) in 150 mL of THF was added MeMgCl (3.0 M in THF, 40 mL, 120 mmol) at −78° C. The reaction was stirred at rt overnight, and quenched with 150 mL of aqueous NH4Cl. The product was extracted with 250 mL of EtOAc, and the extracts were dried over anhydrous MgSO4, and concentrated to give 2-(4-bromophenyl)propan-2-ol, which was used without further purification.

Workup

  1. customquenched with 150 mL of aqueous NH4Cl
  2. extractionThe product was extracted with 250 mL of EtOAc
  3. dry with materialthe extracts were dried over anhydrous MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d8a6daca4a9c417ba0d4b25ca363fbfa
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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