Phenethyl bromide → alpha-Phenethyl-2,4-dichlorobenzyl cyanide

HRID 28265

반응식

HRID 28265 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[CH2:6][C:7]#[N:8].O1CCCC1.[CH2:19](Br)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[CH2:19]([CH:6]([C:7]#[N:8])[C:5]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:4]=1[Cl:3])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 7666Phenethyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 805662,4-Dichlorophenylacetonitrile

생성물 1

HCID 12391165alpha-Phenethyl-2,4-dichlorobenzyl cyanide

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
30 °C

실험 절차

Sodium hydride (0.13 mole as a 50% dispersion in mineral oil) is washed with 100 ml. of dry n-hexane to remove the mineral oil, then blanketed with dry nitrogen and suspended in 250 ml. of freshly distilled tetrahydrofuran. To this sodium hydride suspension is added dropwise at room temperature a solution of 2,4-dichlorobenzyl cyanide (25 g., 0.13 mole) dissolved in 100 ml. of tetrahydrofuran. When the addition is completed, the temperature is maintained at 30° C. for an additional 0.5 hours. A solution of phenethylbromide (26 g., 0.14 mole) is then added dropwise and the resultant reaction mixture is stirred at 40° C. overnight under nitrogen. The reaction mixture is poured into 1 liter of water and extracted with (3×200 ml.) of ether. The combined ether extracts are washed with water, dilute hydrochloric acid, saturated sodium bicarbonate solution, saturated sodium chloride solution and dried over magnesium sulfate. The solvent is evaporated and the crude product distilled (144°-56°/0.03 mm) to give 26.6 g. (70.5%) of product, which is identified by nmr.

후처리

  1. washSodium hydride (0.13 mole as a 50% dispersion in mineral oil) is washed with 100 ml
  2. customof dry n-hexane to remove the mineral oil
  3. dissolutiondissolved in 100 ml
  4. additionWhen the addition
  5. customthe resultant reaction mixture
  6. extractionextracted with (3×200 ml.) of ether
  7. washThe combined ether extracts are washed with water, dilute hydrochloric acid, saturated sodium bicarbonate solution, saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent is evaporated
  10. distillationthe crude product distilled (144°-56°/0.03 mm)
  11. customto give 26.6 g

출처 및 근거

ORD 기록
ord-c3178ad2e2c04db1a384f9147e3a6c47
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04225723

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