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

HRID 619316

反応式

HRID 619316 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 6344Dichloromethane溶媒2 回

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.).

後処理

  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

出典と根拠

ORDレコード
ord-00fd31b661b847418972274702b96000
出典データセット
uspto-grants-1999_09
特許番号
US05958956

関連ノート

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