Hydrochloric Acid → 2-Chloro-3-(cyanomethyl)benzoic acid

HRID 446370ノート

反応式

HRID 446370 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+].Cl.C#N>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

7

反応物 4

HCID 313Hydrochloric AcidHCID 768Hydrogen CyanideHCID 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 [Aromatic Intermediate 11, step a] (13.2 g) in DMF (150 mL) was treated with a solution of potassium cyanide (7.23 g) in water (50 mL) and the resulting solution was stirred at room temperature overnight. The mixture was diluted with water (200 mL) and carefully acidified with concentrated hydrochloric acid (25 mL), venting any liberated HCN through bleach solution via a stream of nitrogen. After being stirred for 2 hours, the aqueous phase was extracted with ethyl acetate (3×250 mL). The combined organic phases were washed with water (3×250 mL) and brine (250 mL), dried over magnesium sulphate, filtered and evaporated to give the subtitled, compound as a white solid. Yield 10.3 g.

後処理

  1. stirringAfter being stirred for 2 hours
  2. extractionthe aqueous phase was extracted with ethyl acetate (3×250 mL)
  3. washThe combined organic phases were washed with water (3×250 mL) and brine (250 mL)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customto give the

出典と根拠

ORDレコード
ord-12c57a74242848ebba9cc1364ce769e6
出典データセット
uspto-grants-2013_07
特許番号
US08476265B2

反応ノート

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