1-Bromo-4-fluorobenzene → 1-Fluoro-4-pentylbenzene

HRID 2395418ノート

反応式

HRID 2395418 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=C.[Mg].Br[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1>O1CCCC1.CCOCC.[Cl-].[Cl-].[Zn+2]>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:11][CH:12]=1

参加物

7

反応物 3

HCID 99931-Bromo-4-fluorobenzeneHCID 759066-Bromo-1-hexeneHCID 5462224Magnesium2 回

生成物 1

HCID 27374481-Fluoro-4-pentylbenzene

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of 6-bromo-1-hexene (10 g), magnesium (1 .5g), and lodoethane (1 drop) in anhydrous tetrahydrofuran was heated at reflux until all of the magnesium dissolved. The resulting Grignard reagent was cooled to about 0° C. and was treated with a 1M solution of ZnCl2 in ether (67 ml), and the mixture was allowed to warm to room temperature over 30 minutes. Tetraids(triphenylphosphine)palladium (0) (3.5 g) and 4-bromofluorobenzene (6.73 ml) were added to the reaction and the mixture was heated to reflux for 1 hour. The mixture was cooled to room temperature, concentrated in vacuo, diluted with hexane, filtered and concentrated once more in vacuo. Chromatography on a silica gel column eluting with ether-hexane (0-5%) afforded 5 g of a colorless oil.

後処理

  1. temperaturewas heated
  2. dissolutiondissolved
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 1 hour
  5. temperatureThe mixture was cooled to room temperature
  6. concentrationconcentrated in vacuo
  7. additiondiluted with hexane
  8. filtrationfiltered
  9. concentrationconcentrated once more in vacuo
  10. washChromatography on a silica gel column eluting with ether-hexane (0-5%)

出典と根拠

ORDレコード
ord-cb752c8c5282404c97ae76b18ebe3c7e
出典データセット
uspto-grants-1998_09
特許番号
US05814651

反応ノート

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