Hydrochloric Acid → 4-Nitrobenzoylacetonitrile

HRID 1860514ノート

反応式

HRID 1860514 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 5914594-Nitrobenzoylacetonitrile

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e56148dc6f2d4fbf9891222ab662e938
出典データセット
uspto-grants-2003_03
特許番号
US06531478B2

反応ノート

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