1,2-Dichloroethane → 2-Chloro-1-(naphthalen-1-yl)ethan-1-one

HRID 274085Notes

Reaction equation

HRID 274085 reaction equation
Br[CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].[Cl:15]CCCl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:15][CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 111,2-DichloroethaneHCID 38305132-Bromo-1-(1-naphthalenyl)ethanone

Product 1

HCID 125874032-Chloro-1-(naphthalen-1-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

A solution of 2-bromoacetylnaphthalene (7.00 g) and tetra-n-butyl ammonium bromide (0.905 g) in 1,2-dichloroethane (226 ml) was refluxed for 3.5 hours, evaporated in vacuo and extracted with dichloromethane. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was washed with n-hexane to afford 2-chloroacetylnaphthalene (5.43 g) as a yellow powder.

Workup

  1. customevaporated in vacuo
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. washThe residue was washed with n-hexane

Sources & evidence

ORD record
ord-968eb1c0ff3e4458a082a1bf005d9257
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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