Acetic Anhydride → HCID 21846387, compound

HRID 343842Notes

Reaction equation

HRID 343842 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].[C:17](OC(=O)C)(=[O:19])[CH3:18]>ClCCCl>[F:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[C:5]([C:17](=[O:19])[CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 6406201,6-difluoronaphthaleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21846387HCID 21846387, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

1,6-Difluoronaphthalene (0.164 g, 1.0 mmol) was dissolved in 1,2-dichloroethane (5 mL) and cooled to 0° C. Aluminum trichloride (0.264 g, 2.0 mmol) was added as a solid to the solution. Acetic anhydride (0.1 mL, 1.0 mmol) was added slowly over 20 minutes to the solution while maintaining a temperature of 0° C. The reaction was poured onto ice-cold 10% aqueous hydrochloric acid and extracted with methylene chloride (2×10 mL). The organic layer was dried over sodium sulfate, concentrated, and purified by column chromatography to give 1-(4,7-difluoronaphth-1-yl)-ethanone as an oil (0.165 g, 80%).

Workup

  1. temperaturewhile maintaining a temperature of 0° C
  2. additionThe reaction was poured onto ice-cold 10% aqueous hydrochloric acid
  3. extractionextracted with methylene chloride (2×10 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-ea9ded2bdf50429f8d67a10a40b9119a
Source dataset
uspto-grants-1999_01
Patent number
US05863924

Reaction notes

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