Dimethylformamide dimethyl acetal → HCID 11737295, compound

HRID 1684869Notes

Reaction equation

HRID 1684869 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])/[CH:9]=[CH:14]/[N:15]([CH3:17])[CH3:16])=[C:4]([OH:11])[CH:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-one

Product 1

HCID 11737295HCID 11737295, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 1-(4-bromo-2-hydroxyphenyl)ethanone (35.8 g, 167 mmol) in dry benzene (800 mL) was added N,N-dimethylformamide dimethylacetal (44 mL, 333 mmol) and the solution was heated at reflux for 4 hrs and concentrated to dryness. The resulting residue was dissolved in dichloromethane (300 mL) and filtered over SiO2. The organic layer was concentrated to afford (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one as a bright yellow solid (31.9 g, 71%). LCMS 270 (M+H); 1H NMR (DMSO-d6) 14.96 (s, 1H), 7.86-7.94 (m, 2H), 6.96-7.02 (dd, 2H), 5.92-5.96 (d, 1H), 3.32 (s, 3H), 3.20 (s, 3H).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 4 hrs
  3. concentrationconcentrated to dryness
  4. dissolutionThe resulting residue was dissolved in dichloromethane (300 mL)
  5. filtrationfiltered over SiO2
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-043bb4e25e214d569c0496be3af4fe54
Source dataset
uspto-grants-2012_04
Patent number
US08147818B2

Reaction notes

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