Bromine → 3-Bromo-2-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

HRID 2186547

반응식

HRID 2186547 반응식
[CH2:1]([C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH3:18])([CH3:17])[CH2:12][CH2:11][C:10]([CH3:20])([CH3:19])[C:9]=2[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:21]Br>C(Cl)(Cl)(Cl)Cl.[Fe]>[Br:21][C:16]1[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:8][C:9]2[C:10]([CH3:19])([CH3:20])[CH2:11][CH2:12][C:13]([CH3:18])([CH3:17])[C:14]=2[CH:15]=1

참가 물질

5

반응물 2

HCID 24408BromineHCID 230025302-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

생성물 1

HCID 110786473-Bromo-2-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene수율 89.7%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 5943Carbon Tetrachloride용매2회

반응 조건

온도
0 °C

실험 절차

A solution of 2-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene (from Example 2.1, 12.1 g) in 80 ml of carbon tetrachloride, containing 327 mg of pulverised iron powder, was cooled to 0° C. and treated dropwise with a solution of 7.84 g of Br2 in 8 ml of carbon tetrachloride. The mixture was stirred at 0° C. for 4 hours. The reaction mixture was filtered and then poured into 200 ml ice/water. Extraction of the biphasic mixture with 3 portions of 100 ml of methylene chloride was followed by a washing of the combined organic extracts with 100 ml of saturated aqueous sodium bicarbonate solution and 100 ml water. The organic phase was dried over MgSO4 and concentrated in vacuo, giving a yellow oil. The crude product was distilled under vacuum, yielding 14 g of a pale yellow oil. B.p. 148° C. at 0.09 bar.

후처리

  1. filtrationThe reaction mixture was filtered
  2. additionpoured into 200 ml ice/water
  3. extractionExtraction of the biphasic mixture with 3 portions of 100 ml of methylene chloride
  4. washa washing of the combined organic extracts with 100 ml of saturated aqueous sodium bicarbonate solution and 100 ml water
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customgiving a yellow oil
  8. distillationThe crude product was distilled under vacuum

출처 및 근거

ORD 기록
ord-ceec1ceecb964160958c887ba43273ea
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06403810B2

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