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

HRID 586647Notes

Reaction equation

HRID 586647 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:6]([CH3:14])([CH2:8][CH2:9][C:10](Cl)([CH3:12])[CH3:11])[CH3:7].[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCOCC.CCCCCC>[Br:15][C:16]1[CH:21]=[C:20]2[C:19](=[CH:18][CH:17]=1)[C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][C:6]2([CH3:14])[CH3:7]

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-tetrahydronaphthaleneYield 83%

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

Aluminum chloride (700 mg, 5.25 mmol) was added slowly to a solution of 2,5-dichloro-2,5-dimethylhexane (11 g, 60 mmol) in bromobenzene (90 mL) at 0° C. After stirred for 20 min, the mixture was diluted with 100 mL of ether:hexane (1:1), washed with ice-water (1×10 mL), 10% HCl (1×10 mL) and brine (1×10 mL), dried (MgSO4) and concentrated to afford a brown oil. The crude was then distilled using Coughler distillation to yield the title compound (13.2 g, 83% yield) as a white solid:

Workup

  1. washwashed with ice-water (1×10 mL), 10% HCl (1×10 mL) and brine (1×10 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto afford a brown oil
  5. distillationThe crude was then distilled
  6. distillationCoughler distillation

Sources & evidence

ORD record
ord-637c68d4018245a8a8e4664c6851ea9f
Source dataset
uspto-grants-2005_08
Patent number
US06936636B2

Reaction notes

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