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

HRID 1637

Reaktionsgleichung

Reaktionsgleichung von HRID 1637
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f15578709608425ca7e804635f32e399
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726191

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