Hydrochloric Acid → 4-Nitrobenzoylacetonitrile

HRID 1860514노트

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HRID 1860514 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4].[C-:14]#[N:15].[Na+].Cl>C(O)C.O>[C:14]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:4])#[N:15]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 668402-Bromo-4'-nitroacetophenone

생성물 1

HCID 5914594-Nitrobenzoylacetonitrile

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

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온도
0 °C

실험 절차

To a solution of 2-bromo-4′-nitroacetophenone (30 g, 0.123 mol) in ethanol (200 mL) at 0° C. was added a solution of NaCN (18 g, 0.368 mol) in H2O (60 mL) dropwise over 1 h. Upon completion of the addition, the mixture was stirred at 0° C. for an additional hour and then diluted with H2O (200 mL). The solution was treated with 1N aq. HCl solution, to a pH of 2, and extracted with CH2Cl2 (2×500 ML). The combined organic layers were dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified by flash chromatography on silica gel eluting with 1:1 hexane/EtOAc to obtain 2-cyano-4′nitroacetophenone as an orange solid.

후처리

  1. additionUpon completion of the addition
  2. extractionextracted with CH2Cl2 (2×500 ML)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified by flash chromatography on silica gel eluting with 1:1 hexane/EtOAc

출처 및 근거

ORD 기록
ord-e56148dc6f2d4fbf9891222ab662e938
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531478B2

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