Ammonium Chloride → 1-(3-Bromophenyl)-2,2-dimethylpropan-1-ol

HRID 546831Notes

Reaction equation

HRID 546831 reaction equation
[C:1]([Mg]Cl)([CH3:4])([CH3:3])[CH3:2].[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12].[Cl-].[NH4+]>O1CCCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH:11]([OH:12])[C:1]([CH3:4])([CH3:3])[CH3:2])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 765833-BromobenzaldehydeHCID 178418310HCID 178418310, compound

Product 1

HCID 574434831-(3-Bromophenyl)-2,2-dimethylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

t-Butylmagnesium chloride (0.93 mol/l solution in tetrahydrofuran, 75.5 mL, 70.26 mmol) was added to a solution of 3-bromobenzaldehyde (10 g, 54.05 mmol) in tetrahydrofuran (100 mL) in a nitrogen atmosphere at −78° C. The mixture was stirred at the same temperature for one hour and then heated to room temperature. 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 filtered, and the solvent was distilled off under reduced pressure to give crude 1-(3-bromo-phenyl)-2,2-dimethyl-propan-1-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. filtrationfiltered
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-25a0da022fc04485a7bd82c0bcbed3fc
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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