3,N-Dimethoxy-N-methyl-5-trifluoromethylbenzamide → 3'-Methoxy-5'-(trifluoromethyl)acetophenone

HRID 657954Notes

Reaction equation

HRID 657954 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:6](N(OC)C)=[O:7].[CH3:19][Mg]Br>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6](=[O:7])[CH3:19])[CH:12]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:14]=1

Participants

4

Reactant 2

HCID 581368103,N-Dimethoxy-N-methyl-5-trifluoromethylbenzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 197023363'-Methoxy-5'-(trifluoromethyl)acetophenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3,N-Dimethoxy-N-methyl-5-trifluoromethylbenzamide (O3.014, 460 mg) was initially charged in THF (15 ml) under at RT Ar dissolved. Thereafter, the mixture was cooled to 0° C., and methylmagnesium bromide (1.5 ml; 3 M in diethyl ether) was added dropwise. Subsequently, the ice bath was removed and the mixture was stirred at RT for 2 h. Then the mixture was admixed with 1 N hydrochloric acid while cooling with ice, diluted with water and extracted three times with EA. The combined EA phases were dried over sodium sulfate, filtered and concentrated. 349 mg of the title compound were isolated.

Workup

  1. dissolutiondissolved
  2. customSubsequently, the ice bath was removed
  3. temperaturewhile cooling with ice
  4. additiondiluted with water
  5. extractionextracted three times with EA
  6. dry with materialThe combined EA phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0ac43b9c91ac49018c1934db01c27699
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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