Ammonium Chloride → 1-(4-Bromophenyl)-2-methylpropan-1-ol
Reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]([Mg]Cl)([CH3:12])[CH3:11].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 4-brombenzaldehyde (27 mmol, 5.0 g) in THF (20 mL) was added at −78° C. a solution of isopropylmagnesium chloride (41 mmol, 20.2 mL, 2M in ether). The mixture was stirred at −78° C. for 1 h and warmed to 0° C. for 1 h. NH4Cl was added an the mixture was extracted with EtOAc. The organic extract was washed with brine, dried and concentrated to an oil. Chromatography (5-15% EtOAc/hexane) gave the desired alcohol.
Workup
- temperaturewarmed to 0° C. for 1 h
- extractionwas extracted with EtOAc
- extractionThe organic extract
- washwas washed with brine
- customdried
- concentrationconcentrated to an oil
Sources & evidence
- ORD record
- ord-184feced80c043bd85c31edc3459bb86
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07279478B2
Reaction notes
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