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

HRID 546822

Reaction equation

HRID 546822 reaction equation
[CH3:1][Li].[CH3:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)=[O:5].[Cl-].[NH4+]>O1CCCC1>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]([OH:5])([CH3:1])[CH3:3])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7466p-BromoacetophenoneHCID 25517Ammonium ChlorideHCID 178418348HCID 178418348, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyllithium (1.10 mol/l solution in diethyl ether, 502 mL, 0.552 mol) was added to a solution of 4-bromoacetophenone (100 g, 0.502 mol) in tetrahydrofuran (500 mL) in a nitrogen atmosphere at −78° C., and the mixture was stirred at the same temperature for one hour. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give crude 2-(4-bromo-phenyl)-propan-2-ol.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ae60c4c0673d4a18a150ebdc63f44cd6
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Linked notes

Loading…