Hydrochloric Acid → 1-[3-Methyl-4-(trifluoromethyl)phenyl]ethan-1-one

HRID 268913Notes

Reaction equation

HRID 268913 reaction equation
CON(C)[C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[C:7]([CH3:15])[CH:6]=1.[CH3:18][Mg]Br.C(OCC)C.Cl>C1COCC1.CCOC(C)=O>[CH3:15][C:7]1[CH:6]=[C:5]([C:4](=[O:16])[CH3:18])[CH:10]=[CH:9][C:8]=1[C:11]([F:14])([F:13])[F:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86086315N-Methoxy-N,3-dimethyl-4-(trifluoromethyl)benzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 574686561-[3-Methyl-4-(trifluoromethyl)phenyl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-methoxy-3,N-dimethyl-4-trifluoromethyl-benzamide from step 7 (16.90 g, 68.36 mmol) in THF (280 mL) at −5° C. was added a 3 M methylmagnesium bromide solution in diethyl ether (45.6 mL, 136.7 mmol). The mixture was stirred at 0° C. for 1 h, then was warmed up to 23° C. and stirring was continued at 23° C. for further 1.5 h under nitrogen atmosphere. Then 1 N HCl (100 mL) was added drop wise to the mixture and stirring was continued for 30 min. The mixture was diluted with EtOAc and the aqueous layer was separated, the organic layer was washed with brine and dried over MgSO4. Removal of the solvent in vacuum left the title compound as a light brown liquid (12.87 g, 93.1%), which was used without further purification. MS (EI) 202.1 [M].

Workup

  1. temperaturewas warmed up to 23° C.
  2. stirringstirring
  3. waitwas continued at 23° C. for further 1.5 h under nitrogen atmosphere
  4. stirringstirring
  5. waitwas continued for 30 min
  6. customthe aqueous layer was separated
  7. washthe organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. customRemoval of the solvent in vacuum
  10. waitleft the title compound as a light brown liquid (12.87 g, 93.1%), which
  11. customwas used without further purification

Sources & evidence

ORD record
ord-1eae5e3deb3d4aa2adbbe47959cb1417
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

Loading…