p-Bromoacetophenone → (2E)-1-(4-Bromophenyl)-3-(dimethylamino)-2-propen-1-one

HRID 878545Notes

Reaction equation

HRID 878545 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH:14](OC)OC)[CH3:13]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])/[CH:9]=[CH:11]/[N:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7466p-BromoacetophenoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 5376915(2E)-1-(4-Bromophenyl)-3-(dimethylamino)-2-propen-1-oneYield 61%

Procedure

A solution of 1-(4-bromophenyl)ethanone (2.0 g, 10 mmol) in DMF-DMA (25 mL) was stirred at 100° C. for 16 h. The solution was concentrated and purified by flash column chromatography (hexanes:EtOAc=4:1˜2:1) to give the title compound (1.57 g, 61%) as an orange-brown solid.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by flash column chromatography (hexanes:EtOAc=4:1˜2:1)

Sources & evidence

ORD record
ord-2c5825c09eee436ca609f4716f9e1283
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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