Réaction #1733

Équation de réaction

2-hexyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene

Br2

→

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

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONthe mixture was poured on to ice
2. 2
   Extractionextracted with diethyl ether
3. 3
   Lavagewashed with bisulphite solution and NaCl soln
4. 4
   Séchage, dried over Na2SO4
5. 5
   Autreevaporated to dryness

Mode opératoire

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.).

Source