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

HRID 1486400Notes

Reaction equation

HRID 1486400 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].[Al+3].[Cl-].[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 45.2%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromonaphthalene (41.4 g, 200 mmol), acetyl chloride (11.3 mL, 160 mmol), nitrobenzene (250 mL) and AlCl3 (28 g, 210 mmol) was stirred for 4 hours at 100° C. (oil bath temperature). The resulting reaction mixture was cooled, poured onto ice/water (100 mL) and filtered. The filtrate was washed with water (100 mL). The solvent (nitrobenzene) was removed by distillation. The resulting residue was crystallized from hexane to afford 18 g of desired product (36% yield). 1-(6-bromonaphthalen-2-yl)ethanone: 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 2.66 (s, 3H) 7.66 (dd, J=8.8, 2.0 Hz, 1H) 7.86 (d, J=8.8 Hz, 1H) 7.94 (d, J=8.8 Hz, 1H) 8.02 (dd, J=8.8, 1.8 Hz, 1H) 8.13 (d, J=2.0 Hz, 1H) 8.53 (d, J=1.8 Hz, 1H).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas cooled
  3. additionpoured onto ice/water (100 mL)
  4. filtrationfiltered
  5. washThe filtrate was washed with water (100 mL)
  6. customThe solvent (nitrobenzene) was removed by distillation
  7. customThe resulting residue was crystallized from hexane

Sources & evidence

ORD record
ord-d054ec11bf3146eb8df456e092a9c1e9
Source dataset
uspto-grants-2016_08
Patent number
US09427428B2

Reaction notes

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