Dimethylformamide dimethyl acetal → (2E)-1-(4-bromo-2-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one

HRID 69102Notes

Reaction equation

HRID 69102 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.CO[CH:16]([N:19]([CH3:21])[CH3:20])OC>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])/[CH:9]=[CH:16]/[N:19]([CH3:21])[CH3:20])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 145036131-(4-Bromo-2-nitrophenyl)ethanone

Product 1

HCID 86694307(2E)-1-(4-bromo-2-nitrophenyl)-3-(dimethylamino)prop-2-en-1-oneYield 88.6%

Conditions

Temperature
90 °C

Procedure

Under a nitrogen atmosphere, a mixture of 3.62 g of 1-(4-bromo-2-nitrophenyl)ethanone and 5.3 g of (dimethoxymethyl)dimethylamine was stirred at 90° C. for 4 hours. The reaction mixture was cooled to room temperature and the precipitated solid was collected by filtration. The obtained solid was washed with diisopropyl ether and dried under reduced pressure to obtain 3.93 g of (2E)-1-(4-bromo-2-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. washThe obtained solid was washed with diisopropyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-a8d3c9035d10428b97516c5c7343b6a5
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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