Bromobenzene → 6-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

HRID 2420658Notes

Reaction equation

HRID 2420658 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:9]([CH3:17])([CH2:11][CH2:12][C:13](Cl)([CH3:15])[CH3:14])[CH3:10].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[C:13]([CH3:15])([CH3:14])[CH2:12][CH2:11][C:9]2([CH3:17])[CH3:10]

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 2266856-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customA 200 ml round-bottomed flask equipped with a stir bar and a reflux condenser
  2. temperatureuntil spontaneous reflux subsides
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc (5×20 ml)
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-db3db0cadda847e3be84a6ece7695dfb
Source dataset
uspto-grants-2011_06
Patent number
US07955852B2

Reaction notes

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