Dibenzofuran → 2-Acetyldibenzofuran

HRID 1781174

반응식

HRID 1781174 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1[C:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[C:18](Cl)(=[O:20])[CH3:19]>ClC(Cl)C>[C:18]([C:6]1[CH:7]=[CH:8][C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[C:13]=2[CH:5]=1)(=[O:20])[CH3:19]

참가 물질

5

반응물 3

HCID 568DibenzofuranHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 2930282-Acetyldibenzofuran수율 28.3%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

Aluminum chloride (23.8 g, 178.4 mmol) was added portionwise to a solution of dibenzofuran (30.0 g, 178.4 mmol) and acetyl chloride (14.0 g, 178.4 mmol) in dichloroethane at 0° C. After 8 hours, the reaction was quenched with 6N HCl. The layers were separated and the methylene chloride layer was dried (MgSO4), filtered and concentrated to provide a yellow solid. The solid was recrystallized 3 times from hexane to provide 10.6 g (28%) of the title compound as a white solid. 1H NMR (CDCl3, 300 MHz) δ 2.7 (s, 3H), 7.4 (dt, J=7.5 Hz, 0.5 Hz, 1H), 7.5 (dt, J=7.5 Hz, 0.5 Hz, 1H), 7.65 (d, J=7.5 Hz, 2H), 8.0 (d, J=7.5 Hz, 1H), 8.15 (dd, J=7.5 Hz, 0.5 Hz), 8.6 (d, J=0.5 Hz). MS (DCl/NH3) m/e 211 (M+H)+.

후처리

  1. customthe reaction was quenched with 6N HCl
  2. customThe layers were separated
  3. dry with materialthe methylene chloride layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide a yellow solid
  7. customThe solid was recrystallized 3 times from hexane

출처 및 근거

ORD 기록
ord-b2b29368f8524ef8a54a46dbbda5d4cb
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05631401

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