Hydrogen Bromide → HCID 14050771, 화합물

HRID 1200296노트

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HRID 1200296 반응식
S(Cl)(Cl)=O.[C:5]([O:8][C:9]1[CH:10]=[C:11]([CH2:19][C:20]([OH:22])=[O:21])[CH:12]=[CH:13][C:14]=1[O:15][C:16](=[O:18])[CH3:17])(=[O:7])[CH3:6].[Br:23]N1C(=O)CCC1=O.Br>C(Cl)(Cl)(Cl)Cl>[Br:23][CH:19]([C:11]1[CH:12]=[CH:13][C:14]([O:15][C:16](=[O:18])[CH3:17])=[C:9]([O:8][C:5](=[O:7])[CH3:6])[CH:10]=1)[C:20]([OH:22])=[O:21]

참가 물질

6

반응물 4

HCID 260Hydrogen BromideHCID 24386Thionyl ChlorideHCID 67184N-bromobutanimideHCID 30208503,4-Diacetoxyphenylacetic acid

생성물 1

HCID 14050771HCID 14050771, 화합물수율 91.5%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매2회

반응 조건

온도
70 °C

실험 절차

Thionyl chloride (60 ml) was added to a suspension of 3,4-diacetoxyphenylacetic acid (51.1 g) in carbon tetrachloride (105 ml) and the mixture was heated at 70° C. for one hour. After cooling to room temperature, N-bromosuccinimide (42.3 g), carbon tetrachloride (105 ml) and a little amount of hydrobromic acid were added, and the mixture was heated for an additional one hour. The resulting mixture was concentrated under reduced pressure, and the residue was redissolved in carbon tetrachloride. After filtering off the insoluble matters, the filtrate ws dissolved in acetone (400 ml) and the pH of the solution was adjusted to 4.0 with saturated sodium bicarbonate aqueous solution under ice cooling. The resulting mixture was extracted with chloroform. The chloroform layer was washed with brine and dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure, giving 61.4 g of the objective compound.

후처리

  1. temperatureAfter cooling to room temperature
  2. temperaturethe mixture was heated for an additional one hour
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. dissolutionthe residue was redissolved in carbon tetrachloride
  5. filtrationAfter filtering off the insoluble matters
  6. dissolutionthe filtrate ws dissolved in acetone (400 ml)
  7. extractionThe resulting mixture was extracted with chloroform
  8. washThe chloroform layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationThe dried solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-dd9ab98846f946feb061dc5b6f6387d7
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04904791

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