1,2-Dichloroethane → 6-Bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

HRID 858272Notes

Reaction equation

HRID 858272 reaction equation
Cl[C:2]([CH3:10])([CH2:4][CH2:5][C:6](Cl)([CH3:8])[CH3:7])[CH3:3].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].ClCCCl.[Cl-].[Al+3].[Cl-].[Cl-]>O>[Br:11][C:12]1[CH:17]=[C:16]2[C:15](=[CH:14][C:13]=1[CH3:18])[C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][C:2]2([CH3:10])[CH3:3]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 72362-BromotolueneHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 100393466-Bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18.31 g (100.0 mmol) of 2,5-dichloro-2,5-dimethylhexane, 17.10 g (100.0 mmol) of 2-bromotoluene and 200 ml of 1,2-dichloroethane are introduced into a three-necked flask under an argon atmosphere. 1.33 g (10.0 mmol) of aluminium chloride are added rapidly in a single portion and the reaction medium is stirred for thirty minutes at room temperature. The reaction medium is poured into water, extracted with dichloromethane and washed with water, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. After recrystallization of the residue from methanol, 17.78 g (63%) of the expected compound are collected in the form of fine white crystals with a melting point of 73° C.

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with water
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customAfter recrystallization of the residue from methanol, 17.78 g (63%) of the expected compound
  7. customare collected in the form of fine white crystals with a melting point of 73° C.

Sources & evidence

ORD record
ord-592b54ede64b4dbb8ac5bfcd345c18b3
Source dataset
uspto-grants-2006_12
Patent number
US07148245B2

Reaction notes

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