p-Bromochlorobenzene → 1-Chloro-4-(2-propyn-1-yl)benzene

HRID 65233

반응식

HRID 65233 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.CO[CH:12]=[C:13]=[CH2:14].[Cl-].[NH4+]>CCOCC.OC(C1C=CC(NS(C)(=O)=O)=CC=1)CN1C=CN=C1>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:14][C:13]#[CH:12])=[CH:4][CH:5]=1

참가 물질

7

반응물 4

HCID 7806p-Bromochlorobenzene2회HCID 25517Ammonium ChlorideHCID 1394031-Methoxypropa-1,2-dieneHCID 5462224Magnesium

생성물 1

HCID 136602551-Chloro-4-(2-propyn-1-yl)benzene

시약·촉매·용매 2

HCID 3283Diethyl Ether용매3회HCID 13763390N-[4-(1-Hydroxy-2-(1H-imidazol-1-yl)ethyl]phenyl]methanesulfonamide용매

실험 절차

In a flask containing 59 g (2.43 mole) magnesium turnings in 500 ml anhydrous ether under an atmosphere of nitroge add slowly a solution of 465 g (2.43 mole) of 4-bromochlorobenzene in 1 liter 4 anhydrous ether. With caution, once the Grignard has started maintain slow reflux until all 4-bromochlorobenzene has been added. Stir an additional hour and then add this Grignard (maintain slow reflux) to a suspension of 170 g (2.43 mole) methoxyallene and 69 g of cuprous bromide in 300 ml anhydrous ether under N2. When addition is complete, stir another 10 minutes and then add saturated ammonium chloride. Decant off the ether solution wash the solid residue with ether (3×50 ml). Combine the ether extracts and wash with 1N HCl, saturated aqueous sodium bicarbonate, water and dry over magnesium sulfate. Evaporate off the ether and distill the residue in vacuo to obtain the title compound (99-105mmHg).

후처리

  1. temperatureWith caution, once the Grignard has started maintain slow
  2. additionhas been added
  3. additionadd
  4. temperaturethis Grignard (maintain slow reflux)
  5. additionWhen addition
  6. stirringstir another 10 minutes
  7. customDecant off the ether solution
  8. washwash the solid residue with ether (3×50 ml)
  9. washCombine the ether extracts and wash with 1N HCl, saturated aqueous sodium bicarbonate, water
  10. dry with materialdry over magnesium sulfate
  11. customEvaporate off the ether
  12. distillationdistill the residue in vacuo

출처 및 근거

ORD 기록
ord-1d42ee52890f4ac9a7be41fcf2c87f49
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04613609

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