Ammonium Chloride → 1-(4-Bromophenyl)-2-methylpropan-1-ol

HRID 1180415Notes

Reaction equation

HRID 1180415 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]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 707414-BromobenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 217141961-(4-Bromophenyl)-2-methylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperaturewarmed to 0° C. for 1 h
  2. extractionwas extracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. customdried
  6. 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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