Potassium Cyanide → 2-Chloro-3-(cyanomethyl)benzoic acid

HRID 471182ノート

反応式

HRID 471182 の反応式
Br[CH2:2][C:3]1[C:4]([Cl:12])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[C-:13]#[N:14].[K+]>CN(C=O)C.O>[Cl:12][C:4]1[C:3]([CH2:2][C:13]#[N:14])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

参加物

5

反応物 2

HCID 9032Potassium CyanideHCID 202214903-(Bromomethyl)-2-chlorobenzoic acid

生成物 1

HCID 579893812-Chloro-3-(cyanomethyl)benzoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3-(bromomethyl)-2-chlorobenzoic acid (6.39 g) in DMF (75 mL) was treated with a solution of potassium cyanide (3.34 g) in water (25 mL) and the resulting solution was stirred at room temperature overnight. The mixture was diluted with water and extracted twice with ethyl acetate. The organic phases were discarded, whilst the aqueous phase was carefully acidified with concentrated hydrochloric acid (25 mL), venting any liberated HCN through a bleach solution via a stream of nitrogen. After being stirred for 2 hours, the aqueous phase was extracted twice more with ethyl acetate. The combined organic phases were washed three times with water, once with brine, then dried over anhydrous magnesium sulphate and concentrated in vacuo to afford the crude subtitled compound as a pale brown solid. Yield 4.12 g.

後処理

  1. extractionextracted twice with ethyl acetate
  2. stirringAfter being stirred for 2 hours
  3. extractionthe aqueous phase was extracted twice more with ethyl acetate
  4. washThe combined organic phases were washed three times with water
  5. dry with materialonce with brine, then dried over anhydrous magnesium sulphate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d19e8d937a874c1c83985ff7a18d0fb7
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

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