Hydrochloric Acid → 1-Benzoylnaphthalene

HRID 1275418

반응식

HRID 1275418 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.II.[C:10]1([C:20]#N)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.Cl.C([O:25]CC)C>[Mg].C(Cl)Cl.O>[C:20]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)(=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 3283Diethyl Ether2회HCID 68461-NaphthalenecarbonitrileHCID 7961Bromobenzene3회

생성물 1

HCID 695031-Benzoylnaphthalene수율 29%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 5462224Magnesium용매

실험 절차

To 10.3 g (65 mMol) of bromobenzene in 50 mL of diethyl ether, magnesium turnings were added. The reaction was initiated by adding a few crystals of iodine to about 5 mL of the bromobenzene solution, and warming gently. The remainder of the bromobenzene was then added at such a rate as to maintain a mild reflux. When the reaction had abated, 1-naphthonitrile was added slowly in 50 mL of diethyl ether. The mixture was allowed to stir at room temperature overnight. Water was added, and the mixture acidified to pH 1 with concentrated hydrochloric acid. Methylene chloride was added and the mixture was heated under reflux overnight. The layers were separated, and the organic layer was washed with brine and dried over magnesium sulfate. The subtitled product was crystallized from methylene chloride/hexane, then further purified by medium pressure column chromatography on silica gel, eluting with ethyl acetate:hexane/5:95. The desired product was obtained as a white crystalline solid (4.38 g; 29% yield).

후처리

  1. temperaturewarming gently
  2. temperatureto maintain a mild reflux
  3. temperaturethe mixture was heated
  4. temperatureunder reflux overnight
  5. customThe layers were separated
  6. washthe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customThe subtitled product was crystallized from methylene chloride/hexane
  9. customfurther purified by medium pressure column chromatography on silica gel
  10. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-449c62ea40fa4d84965ad289fcaef310
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06160175

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