Dimethylamine → 2-Dimethylamino-4'-difluoromethoxyacetophenone

HRID 1031237Notes

Reaction equation

HRID 1031237 reaction equation
[CH3:1][NH:2][CH3:3].Br[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([F:17])[F:16])=[CH:10][CH:9]=1)=[O:7]>C(Cl)Cl>[CH3:1][N:2]([CH3:3])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([F:17])[F:16])=[CH:10][CH:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 7034962-Bromo-1-(4-(difluoromethoxy)phenyl)ethan-1-one

Product 1

HCID 189809272-Dimethylamino-4'-difluoromethoxyacetophenoneYield 44.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To 7.5 g (165 mmole) of anhydrous dimethylamine in 50 ml of methylene chloride and cooled to -30° C. was added a solution of 20 g (664 mmole) of 2-bromo-4'-difluoromethoxyacetophenone in 50 ml of methylene chloride. After the addition was complete the reaction was allowed to warm to 20° C. Concentration in vacuo, partitioning between diethyl ether and 1M aqueous sodium hydroxide, washing with brine, drying over anhydrous magnesium sulfate, and reconcentration in vacuo yielded 16.8 g of 2-dimethylamino-4'-difluoromethoxyacetophenone, an oil.

Workup

  1. additionAfter the addition
  2. concentrationConcentration in vacuo
  3. custompartitioning between diethyl ether and 1M aqueous sodium hydroxide
  4. washwashing with brine
  5. dry with materialdrying over anhydrous magnesium sulfate, and reconcentration in vacuo

Sources & evidence

ORD record
ord-e1945386f85048898b7fe2905c06b3a4
Source dataset
uspto-grants-1992_04
Patent number
US05109014

Reaction notes

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