Reaction #2507840

Reaction equation

bromobenzene

2,5-dichloro-2,5-dimethyl hexane

Aluminum chloride

→

6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherA 200 ml round-bottomed flask equipped with a stir bar and a reflux condenser
2. 2
   Temperatureuntil spontaneous reflux subsides
3. 3
   Otherthe layers were separated
4. 4
   ExtractionThe aqueous layer was extracted with EtOAc (5×20 ml)
5. 5
   WashThe combined organic layer was washed with water and brine
6. 6
   Dryingdried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated

Procedure

A 200 ml round-bottomed flask equipped with a stir bar and a reflux condenser was charged with a solution of bromobenzene (109 mmol, 17 ml) and 2,5-dichloro-2,5-dimethyl hexane (10 grams, 54.6 mmol) in dichloromethane (30 ml). Aluminum chloride (1.45 grams, 10.9 mmol) was added to the solution slowly, until spontaneous reflux subsides. After stirring for 10-15 minutes at room temperature, the reaction was poured into ice water (30 ml) and the layers were separated. The aqueous layer was extracted with EtOAc (5×20 ml). The combined organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated, to yield a 6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene product.

Source