Hydrochloric Acid → (4-Bromophenyl)(4-fluorophenyl)methanone

HRID 1033975

반응식

HRID 1033975 반응식
[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11](C#CC3C=CC=CC=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.FC1C=CC=CC=1.[Br:31]C1C=CC(CCl)=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[Br:31][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=2)=[O:7])=[CH:9][CH:10]=1

참가 물질

6

반응물 5

HCID 313Hydrochloric AcidHCID 10008FluorobenzeneHCID 68528p-Bromobenzyl chlorideHCID 40956574-Fluoro-4'-(phenylethynyl)benzophenoneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 74951(4-Bromophenyl)(4-fluorophenyl)methanone수율 86%

실험 절차

Synthesis of 4-fluoro-4'-phenylethynylbenzophenone In a 250 mL flask equipped with a nitrogen inlet, overhead stirring assembly, and reflux condenser was placed fluorobenzene (117 g, 1.2 mol), and 4-bromobenzyl chloride (39.8 g, 0.181 mol). The mixture was cooled to 0° C. an anhydrous aluminum chloride (27 g, 0.20 mol) was added. The mixture was stirred at 23° C. for 16 hours. The resulting slurry was poured into 2 L of acidic (HCl) water. The organics were extracted with methylene chloride, and dried over magnesium sulfate. The slurry was filtered and the methylene chloride was removed under reduced pressure. Recrystallization from ethanol afforded 43.3 g (86%) of 4-bromo-4'-fluorobenzophenone as white crystals: mp 106°-107° C. (Lit 107°-108° C.).

후처리

  1. customequipped with a nitrogen inlet
  2. temperaturereflux condenser
  3. additionwas added
  4. stirringThe mixture was stirred at 23° C. for 16 hours
  5. extractionThe organics were extracted with methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe slurry was filtered
  8. customthe methylene chloride was removed under reduced pressure
  9. customRecrystallization from ethanol

출처 및 근거

ORD 기록
ord-d03901bcb5e142568d70254e005582fc
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05312994

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