Acetyl chloride → 1-(6-Bromonaphthalen-2-yl)ethanone

HRID 2408327Notes

Reaction equation

HRID 2408327 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[C:12](Cl)(=[O:14])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](=[O:14])[CH3:13])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 113722-BromonaphthaleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 124330821-(6-Bromonaphthalen-2-yl)ethanoneYield 42%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromonaphthalene (950 g, 4589 mmol), acetyl chloride (260 mL, 4589 mmol), nitrobenzene (6000 mL) and aluminum chloride (642.2 g, 4818 mmol) was stirred for 4 hours at 100° C. The mixture was poured onto ice water, the resulting slurry was filtrated and the organic phase separated from the filtrate. The organic phase was washed with water (2000 mL), dried over Na2SO4 and filtrated. The solvent was removed by distillation. The residue was re-crystallized from a solution of hexane:ethyl acetate (10:1) resulting in 1-(6-bromonaphthalen-2-yl)ethanone (480 g, 42% yield).

Workup

  1. additionThe mixture was poured onto ice water
  2. filtrationthe resulting slurry was filtrated
  3. customthe organic phase separated from the filtrate
  4. washThe organic phase was washed with water (2000 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltrated
  7. customThe solvent was removed by distillation
  8. customThe residue was re-crystallized from a solution of hexane:ethyl acetate (10:1)

Sources & evidence

ORD record
ord-97d717ca04d14e7db935c22b945621a1
Source dataset
uspto-grants-2014_08
Patent number
US08815849B2

Reaction notes

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