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Dibenzofuran → Dibenzofuran-2-ylethan-2-one

HRID 17746
Notes
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Reaction equation

HRID 17746 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:18](Cl)(=[O:20])[CH3:19]>C(Cl)Cl>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:19][CH:18]=[O:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

HCID 13477039Dibenzofuran-2-ylethan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of dibenzofuran (0.5 mmol) in anhydrous DCM was cooled to 0° C. AlCl3 (1.5 eq., 0.75 mmol) was added followed by a slow addition of acetyl chloride (1.5 eq., 0.75 mmol). The reaction mixture was stirred at 0° C. for 2-3 h or until the completion of reaction. The product was extracted with DCM and washed with saturated sodium bicarbonate solution. The organic layer was dried over anhydrous sodium sulfate and concenterated in vacuo to give dibenzofuran-2-ylethan-2-one.

Workup

  1. extractionThe product was extracted with DCM
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-dde33f8697034d5b92476b07d2715063
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737285B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes