Water → 2-(3,4-Dichlorophenyl)-3-hydroxy-4-(methylcarbonyl)thiophene

HRID 239215

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HRID 239215 반응식
C(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2(Cl)[CH:17]([OH:18])[C:16]([C:19]([CH3:21])=[O:20])=[C:15](Cl)[S:14]2)[CH:9]=[CH:10][C:11]=1[Cl:12].S(Cl)(Cl)(=O)=O.O>CC(O)C>[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2[S:14][CH:15]=[C:16]([C:19]([CH3:21])=[O:20])[C:17]=2[OH:18])[CH:9]=[CH:10][C:11]=1[Cl:12]

참가 물질

6

반응물 4

HCID 962WaterHCID 6212Chloroform2회HCID 24648Sulfuryl chlorideHCID 671597712-(3,4-Dichlorophenyl)-3-hydroxy-4-methylcarbonyl-2,5-dichlorothiophene

생성물 1

HCID 442072882-(3,4-Dichlorophenyl)-3-hydroxy-4-(methylcarbonyl)thiophene수율 77.8%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
-20 °C

실험 절차

A chloroform (967 mL) solution of 2-(3,4-dichlorophenyl)-3-hydroxy-4-methylcarbonyl-2,5-dichlorothiophene (96.7 g, 221 mmol, purity: 63%) was cooled to −18° C., and to this solution, a chloroform (193 mL) solution of sulfuryl chloride (19.5 mL, 1.15 equivalent amounts) was dropwise added over a period of 20 minutes, followed by stirring at −20° C. for 1 hour. The temperature of the solution was raised to 0° C., and water (193 mL) was dropwise added over a period of 5 minutes, followed by liquid separation. The obtained chloroform solution was sequentially washed with water, a saturated salt solution, a saturated sodium hydrogencarbonate aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off to obtain a crude product. To the obtained crude product, 2-propanol (967 mL) was added, followed by stirring at 5° C. for 1 hour. The formed crystals were subjected to filtration to give the desired product as a pale yellow solid (49.4 g, yield: 51%).

후처리

  1. temperatureThe temperature of the solution was raised to 0° C.
  2. customfollowed by liquid separation
  3. washThe obtained chloroform solution was sequentially washed with water
  4. dry with materiala saturated salt solution, a saturated sodium hydrogencarbonate aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. distillationthe solvent was distilled off
  7. customto obtain a crude product
  8. additionwas added
  9. stirringby stirring at 5° C. for 1 hour
  10. filtrationThe formed crystals were subjected to filtration

출처 및 근거

ORD 기록
ord-fffe37e1d30e4993915eeef48515b46c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642786B2

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