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

HRID 619316

반응식

HRID 619316 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 6344Dichloromethane용매2회

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-00fd31b661b847418972274702b96000
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05958956

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