Iodine → HCID 178447835, 화합물

HRID 2309304노트

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HRID 2309304 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([F:14])[CH:3]=1.[Mg].II.[CH2:18]([C@H:21]1[CH2:26][CH2:25][C@H:24](CC(Cl)=O)[CH2:23][CH2:22]1)[CH2:19][CH3:20]>O1CCCC1.O>[F:14][C:4]1[CH:3]=[C:2]([C@H:24]2[CH2:25][CH2:26][C@H:21]([CH2:18][CH2:19][CH3:20])[CH2:22][CH2:23]2)[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

7

반응물 4

HCID 807IodineHCID 5210634-Bromo-2-fluoro-1,1'-biphenylHCID 5462224MagnesiumHCID 178447993HCID 178447993, 화합물

생성물 1

HCID 178447835HCID 178447835, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

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온도
-60 °C

실험 절차

A solution of 4-bromo-2-fluorobiphenyl (38.1 gram) in tetrahydrofuran (60 ml) was added over 20 minutes to magnesium turnings (4 gram) suspended in tetrahydrofuran (20 ml), reaction being initiated by adding a crystal of iodine and warming as usual. This Grignard reagent was now added to a solution of trans-4-propylcyclohexylacetyl chloride (40 gram) and cuprous chloride (0.4 gram) in tetrahydrofuran (200 ml) with stirring at -60° C. over 90 minutes. After allowing to warm to room temperature over two hours, the mixture was decomposed with water and the product extracted with petroleum ether (bpt. 60°-80°). The crude material was recrystallized twice from ethanol at 5° C. to give the product (20.6 gram, 40% theory), m.p. 96.5°-97.3° C., which was found to be 99.6 pure by glc.

후처리

  1. customreaction being
  2. temperaturewarming as usual
  3. temperatureto warm to room temperature over two hours
  4. extractionthe product extracted with petroleum ether (bpt. 60°-80°)
  5. customThe crude material was recrystallized twice from ethanol at 5° C.
  6. customto give the product (20.6 gram, 40% theory), m.p. 96.5°-97.3° C., which

출처 및 근거

ORD 기록
ord-cff131191944477eaa53b0f9fa9fe91f
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04695131

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