Tetrahydrothiophene → 2-Bromo-1-(phenanthren-2-YL)ethan-1-one

HRID 1421205노트

반응식

HRID 1421205 반응식
[SH3+].S1CCCC1.[C:7]([C:10]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:12]=2[CH:11]=1)(=[O:9])[CH3:8].[Br:24]Br>C(Cl)Cl.C(OCC)C>[Br:24][CH2:8][C:7]([C:10]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:12]=2[CH:11]=1)=[O:9]

참가 물질

7

반응물 4

HCID 1127TetrahydrothiopheneHCID 24408Bromine2회HCID 80060Methyl 2-phenanthryl ketoneHCID 3015009Sulfonium

생성물 1

HCID 187804062-Bromo-1-(phenanthren-2-YL)ethan-1-one

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

Preparation of a sulfonium salt according to Formula 3 wherein X- is CF3SO3- and R1, R2, and S combined are tetrahydrothiophene is as follows. To a stirred solution of 5 grams (22.6 mM) of 2-acetylphenanthrene in a mixture of 30 ml of methylene chloride and 30 ml of diethyl ether cooled in an ice/acetone bath was added 3.5 grains (22 mM) of bromine dropwise over 15 minutes. The red bromine color was immediately discharged upon addition to the stirred solution. The cooling bath was removed and the stirred mixture warmed to room temperature over 30 minutes, then the mixture was stirred at room temperature for 2 hours. The reaction mixture was stripped of solvent on a rotary evaporator, then was suspended in 50 ml diethyl ether and evaporated to dryness. This process was repeated twice more to remove the byproduct hydrogen bromide from the solid product. The residual solid was triturated with 15 ml cold diethyl ether, filtered, and dried in a vacuum oven to yield 4.35 grams of 2-(bromoacetyl)-phenanthrene.

후처리

  1. temperaturecooled in an ice/acetone bath
  2. customThe cooling bath was removed
  3. customThe reaction mixture was stripped of solvent on a rotary evaporator
  4. customevaporated to dryness
  5. customto remove the byproduct hydrogen bromide from the solid product
  6. customThe residual solid was triturated with 15 ml cold diethyl ether
  7. filtrationfiltered
  8. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-fb7ad6239cee418ab2a2dfc7c9484093
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06074800

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