Hydrochloric Acid → 5-(4-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one

HRID 532534

반응식

HRID 532534 반응식
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:9])[CH2:7][CH2:8][C:2]1=2.[H-].[Na+].C1([O:18][C:19](=O)[C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)C=CC=CC=1.Cl>C1COCC1.O>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]([CH:7]2[CH2:8][C:2]3[S:1][CH:5]=[CH:4][C:3]=3[C:6]2=[O:9])=[O:18])=[CH:21][CH:22]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 530840Phenyl 4-bromobenzoateHCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-one

생성물 1

HCID 866991945-(4-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one수율 70%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
100 °C

실험 절차

5,6-Dihydro-cyclopenta[b]thiophen-4-one (3.34 g, 24.2 mmol) in 40 mL of THF was treated with NaH (60 percent, 1.45 g, 36.3 mmol). After the addition of 4-Bromo-benzoic acid phenyl ester (6.7 g, 24.2 mmol), the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was extracted with ethyl acetate. The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(4-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (5.4 g, 16.9 mmol) as yellow solid in 70% yield.

후처리

  1. temperatureThe solution was cooled to room temperature
  2. extractionwas extracted with ethyl acetate
  3. customThe organic layer was collected
  4. dry with materialdried over MgSO4(s)
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant precipitate was collected
  7. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-c0aa556a7a7648fcb7200d401f633a8e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853207B2

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