反応 #1733

反応方程式

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

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   workup.ADDITIONthe mixture was poured on to ice
2. 2
   抽出extracted with diethyl ether
3. 3
   洗浄washed with bisulphite solution and NaCl soln
4. 4
   乾燥, dried over Na2SO4
5. 5
   その他evaporated to dryness

実験手順

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.).

出典