تفاعل #1772051

معادلة التفاعل

1-(4-bromo-2-hydroxyphenyl)ethanone

N,N-dimethylformamide dimethylacetal

→

(E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one

المردود 71.0%

المذيبات

benzene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe solution was heated
2. 2
   درجة الحرارةat reflux for 4 hrs
3. 3
   تركيزconcentrated to dryness
4. 4
   workup.DISSOLUTIONThe resulting residue was dissolved in dichloromethane (300 mL)
5. 5
   ترشيحfiltered over SiO2
6. 6
   تركيزThe organic layer was concentrated

الإجراء التجريبي

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).

المصدر