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

HRID 1380344

反応式

HRID 1380344 の反応式
[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

参加物

7

反応物 4

HCID 7806p-Bromochlorobenzene2 回HCID 25517Ammonium ChlorideHCID 1394031-Methoxypropa-1,2-dieneHCID 5462224Magnesium

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒3 回HCID 13763390N-[4-(1-Hydroxy-2-(1H-imidazol-1-yl)ethyl]phenyl]methanesulfonamide溶媒

実験手順

In a flask containing 59 g (2.43 mole) magnesium turnings in 500 ml anhydrous ether under an atmosphere of nitrogen, and 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 (99-105 mmHg).

後処理

  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

出典と根拠

ORDレコード
ord-4aa74c6da4be459394e1d919e2ca96a0
出典データセット
uspto-grants-1986_04
特許番号
US04581370

関連ノート

読み込み中…