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

HRID 2395418노트

반응식

HRID 2395418 반응식
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

참가 물질

7

반응물 3

HCID 99931-Bromo-4-fluorobenzeneHCID 759066-Bromo-1-hexeneHCID 5462224Magnesium2회

생성물 1

HCID 27374481-Fluoro-4-pentylbenzene

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-cb752c8c5282404c97ae76b18ebe3c7e
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05814651

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