Reaction #84033

Reaction equation

2-bromonaphthalene

acetyl chloride

AlCl3

→

desired product

Yield 45.2%

1-(6-bromonaphthalen-2-yl)ethanone

Yield 45.2%

Solvents

nitrobenzene

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   Temperaturewas cooled
3. 3
   workup.ADDITIONpoured onto ice/water (100 mL)
4. 4
   Filtrationfiltered
5. 5
   WashThe filtrate was washed with water (100 mL)
6. 6
   OtherThe solvent (nitrobenzene) was removed by distillation
7. 7
   OtherThe resulting residue was crystallized from hexane

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).

Source