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

HRID 1417679Notes

Reaction equation

HRID 1417679 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.[Cl-].[Al+3].[Cl-].[Cl-].[C:16](Cl)(=[O:18])[CH3:17]>[N+](C1C=CC=CC=1)([O-])=O>[C:16]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[CH:8]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

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

Product 1

HCID 124330821-(6-Bromonaphthalen-2-yl)ethanoneYield 43.6%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

To a cold (10° C.) mixture of 44.0 g (0.212 mol) of 2-bromonaphthalene and 34.0 g (0.255 mol) of aluminum chloride in 400 ml of nitrobenzene was added 21.0 g (267 mmol) of acetyl chloride. The mechanically stirred reaction mixture was warmed to room temperature, and heated to 40° C. for 18 hours. After cooling to 0° C. in an ice bath, the reaction was quenched by the addition of 12M HCl (70 ml). The layers were separated and the organic phase was washed with water and dilute aqueous Na2CO3. Kugelrohr distillation, followed by recrystallization from 10% EtOAc-hexane yielded 23 g of the title compound as a tan solid. 1H NMR (CDCl3): δ 8.44 (1H, br s), 8.04-8.10 (2H, m), 7.85 (1H, d, J=8.5 Hz), 7.82 (1H, d, J=8.8 Hz), 7.64 (1H, d, J=8.8 Hz), 2.73 (3H, s). 6-bromo-2-naphthalenecarboxylic acid (Compound M)

Workup

  1. customThe mechanically stirred reaction mixture
  2. temperatureheated to 40° C. for 18 hours
  3. temperatureAfter cooling to 0° C. in an ice bath
  4. customthe reaction was quenched by the addition of 12M HCl (70 ml)
  5. customThe layers were separated
  6. washthe organic phase was washed with water and dilute aqueous Na2CO3
  7. distillationKugelrohr distillation
  8. customfollowed by recrystallization from 10% EtOAc-hexane

Sources & evidence

ORD record
ord-b70c216b36b9407a9a507663282004ee
Source dataset
uspto-grants-1999_03
Patent number
US05877207

Reaction notes

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