Iodine → HCID 178447835、化合物

HRID 2309304ノート

反応式

HRID 2309304 の反応式
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

参加物

7

反応物 4

HCID 807IodineHCID 5210634-Bromo-2-fluoro-1,1'-biphenylHCID 5462224MagnesiumHCID 178447993HCID 178447993、化合物

生成物 1

HCID 178447835HCID 178447835、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cff131191944477eaa53b0f9fa9fe91f
出典データセット
uspto-grants-1987_09
特許番号
US04695131

反応ノート

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