Hydrochloric Acid → 1-(3-Bromophenyl)propan-2-one

HRID 1684008Notes

Reaction equation

HRID 1684008 reaction equation
C[Al](C)C.[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[CH2:9]C#N.Cl.C([O:19][CH2:20][CH3:21])(=O)C>C1(C)C=CC=CC=1>[Br:5][C:6]1[CH:7]=[C:8]([CH2:9][C:20](=[O:19])[CH3:21])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 36023(3-Bromophenyl)acetonitrileHCID 16682925Trimethylaluminum

Product 1

HCID 27340931-(3-Bromophenyl)propan-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

Trimethylaluminium in toluene (30 mL, 2M) was added to a -78° C. solution of m-bromobenzyl cyanide (3.92 g, 20 mmol) in toluene (20 mL) and the mixture was slowly warmed up and refluxed for 12 h. After being cooled to 0° C., the solution was carefully added to crushed ice and made acidic with 6N HCl. Ethyl acetate was added and the mixture was vigorously stirred for 1 h. The organic layer was washed with NaHCO3, brine and dried with MgSO4. Removal of the solvent left an oil (4.53 g) which was used as such in the next step.

Workup

  1. temperaturethe mixture was slowly warmed up and
  2. temperaturerefluxed for 12 h
  3. additionthe solution was carefully added
  4. customto crushed ice
  5. washThe organic layer was washed with NaHCO3, brine
  6. dry with materialdried with MgSO4
  7. customRemoval of the solvent
  8. waitleft an oil (4.53 g) which

Sources & evidence

ORD record
ord-fecbd5efd5dc4cf4a67fe196e25b4c18
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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