Hydrochloric Acid → 1,3-Bis(4-fluorobenzoyl)benzene

HRID 1885660

반응식

HRID 1885660 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:15])[C:6]1[CH:14]=[CH:13][CH:12]=[C:8]([C:9](Cl)=[O:10])[CH:7]=1.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:5]([C:6]2[CH:14]=[CH:13][CH:12]=[C:8]([C:9](=[O:10])[C:21]3[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=3)[CH:7]=2)=[O:15])=[CH:20][CH:19]=1

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 7451Isophthaloyl chlorideHCID 10008FluorobenzeneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 6882631,3-Bis(4-fluorobenzoyl)benzene수율 81%

실험 절차

Anhydrous aluminum chloride (160.0 g, 1.20 mol) was added to a stirred solution of isophthaloyl chloride (101.5 g, 0.50 mol) dissolved in fluorobenzene (480.5 g, 5.0 mol) over a five to ten minute period. The mixture was stirred at room temperature for one hour and then maintained at 70°-80° C. for four hours. After cooling, the reaction mixture was poured onto approximately 2000 g of ice containing 100 mL of concentrated hydrochloric acid. The resulting suspension was separated by decantation and washed several times with water. The organic layer was distilled to remove excess fluorobenzene and the solid residue was collected by filtration, washed with water, and dried at 100° C. The crude solid was recrystallized from approximately 1000 mL of toluene to afford 130.5 g (81% yield) of 1,3-bis(4-fluorobenzoyl)benzene; m.p. 177.5°-178.5° C.; 1H NMR (CDCl3) δ 6.8-8.3 (m, 12H, aromatic). Anal. Calcd. for C20H12F2O2 : C, 74.53%; H, 3.75%; F, 11.79%. Found: C, 74.33%; H, 3.59%; F, 11.42%.

후처리

  1. temperaturemaintained at 70°-80° C. for four hours
  2. temperatureAfter cooling
  3. customThe resulting suspension was separated by decantation
  4. washwashed several times with water
  5. distillationThe organic layer was distilled
  6. customto remove excess fluorobenzene
  7. filtrationthe solid residue was collected by filtration
  8. washwashed with water
  9. customdried at 100° C
  10. customThe crude solid was recrystallized from approximately 1000 mL of toluene

출처 및 근거

ORD 기록
ord-bf9ed53aebce45c4bbc1fbd113e2f42e
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05145942

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