Dibenzofuran → 2-Acetyldibenzofuran

HRID 1781174

反応式

HRID 1781174 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 2930282-Acetyldibenzofuran収率 28.3%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-b2b29368f8524ef8a54a46dbbda5d4cb
出典データセット
uspto-grants-1997_05
特許番号
US05631401

関連ノート

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