Ethanol → Ethyl 5-bromo-3-methylthiophene-2-carboxylate

HRID 1465934

반응식

HRID 1465934 반응식
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[C:4]([CH3:10])[CH:3]=1.[CH2:11](O)[CH3:12]>S(Cl)(Cl)=O>[CH2:11]([O:8][C:7]([C:5]1[S:6][C:2]([Br:1])=[CH:3][C:4]=1[CH3:10])=[O:9])[CH3:12]

참가 물질

4

반응물 2

HCID 702EthanolHCID 181766635-Bromo-3-methylthiophene-2-carboxylic acid

생성물 1

HCID 60052343Ethyl 5-bromo-3-methylthiophene-2-carboxylate

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

반응 조건

온도
0 °C

실험 절차

5-Bromo-3-methyl-thiophene-2-carboxylic acid (example 1.b, 10.0 g, 45.2 mmol) was suspended in 40 mL of thionyl chloride. The mixture was heated at reflux temperature for 1 hour and then cooled to 0° C. with an external ice bath. Cold ethyl alcohol (150 mL) was carefully added, and the solution was heated at reflux temperature for 16 hours. Under reduced pressure, the solution was concentrated to ca. one third of the original volume and then diluted with ethyl acetate and washed successively twice with saturated sodium bicarbonate solution, and once with brine. The organic fractions were dried over anhydrous sodium sulfate and concentrated to 7.9 g of a yellow oil: 1H NMR (CDCl3, 200 MHz): δ=6.87 (s, 1H), 4.34-4.23 (q, 1H, J=7.0 Hz), 2.50 (s, 3H), 1.39-1.32 (t, 3H, J=7.0 Hz).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 1 hour
  3. temperaturethe solution was heated
  4. temperatureat reflux temperature for 16 hours
  5. concentrationUnder reduced pressure, the solution was concentrated
  6. additiondiluted with ethyl acetate
  7. washwashed successively twice with saturated sodium bicarbonate solution
  8. dry with materialThe organic fractions were dried over anhydrous sodium sulfate
  9. concentrationconcentrated to 7.9 g of a yellow oil

출처 및 근거

ORD 기록
ord-f3054673d7b74ef49f7f4a610810f31b
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000006B2

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