Bromine → 3-Bromo-2-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

HRID 398304

Reaction equation

HRID 398304 reaction equation
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:9][CH:10]=2)[C:5]([CH3:19])([CH3:18])[CH2:4][CH2:3]1.[Br:21]Br>C(Cl)(Cl)(Cl)Cl.[Fe]>[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[C:9]([Br:21])[CH:10]=2)[C:5]([CH3:19])([CH3:18])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 24408BromineHCID 230025302-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

Product 1

HCID 110786473-Bromo-2-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthaleneYield 100.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

10 g of 1,1,4,4-tetramethyl-6-hexyl-1,2,3,4-tetrahydro-naphthalene were dissolved in 100 ml of carbon tetrachloride and, after the addition of a spatula tip of iron powder, treated dropwise at 0° C. with 6.4 g of bromine. After stirring at 0° C. for 3 hours the reaction mixture was poured into ice-water, extracted with ether and, after drying over sodium sulphate, evaporated. The crude product was purified by filtration over a silica gel column (eluent hexane/ethyl acetate=9:1) and gave 13 g of 1,1,4,4-tetramethyl-6-hexyl-7-bromo-1,2,3,4-tetrahydro-naphthalene as a pale yellow oil.

Workup

  1. extractionextracted with ether
  2. dry with materialafter drying over sodium sulphate
  3. customevaporated
  4. filtrationThe crude product was purified by filtration over a silica gel column (eluent hexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-8cb4d38fa1e4476ea8525ec84e86dc5b
Source dataset
uspto-grants-2003_08
Patent number
US06610877B1

Linked notes

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