Bromine → 2-bromo-3-hexyl-5,5-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene

HRID 1637

Reaction equation

HRID 1637 reaction equation
[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]([CH3:18])([CH3:17])[C:11]=2[CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:20]Br>C(Cl)Cl.[Fe]>[Br:20][C:8]1[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:19][C:11]2[C:12]([CH3:18])([CH3:17])[CH2:13][CH2:14][CH2:15][CH2:16][C:10]=2[CH:9]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 218467162-hexyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene

Product 1

HCID 218467192-bromo-3-hexyl-5,5-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent2×

Procedure

This 3.08 g of 2-hexyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene were dissolved in 35 ml of CH2Cl2, treated at 0° with a spatula tip of Fe powder and then reacted with a solution of 0.67 ml of Br2 (1.1 eq.) in 5 ml of CH2Cl2. After 30 min., the mixture was poured on to ice, extracted with diethyl ether, washed with bisulphite solution and NaCl soln., dried over Na2SO4 and evaporated to dryness. Flash chromatography on SiO2 (hexane) gave 3.21 g of 2-bromo-3-hexyl-5,5-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene as a colorless oil (GC purity: 82%, moreover 2% ed., 2.6% regioisomer, 8.3% dibromo compound and further prod.).

Workup

  1. additionthe mixture was poured on to ice
  2. extractionextracted with diethyl ether
  3. washwashed with bisulphite solution and NaCl soln
  4. dry with material, dried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f15578709608425ca7e804635f32e399
Source dataset
uspto-grants-1998_03
Patent number
US05726191

Linked notes

Loading…