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

HRID 471182Notes

Reaction equation

HRID 471182 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d19e8d937a874c1c83985ff7a18d0fb7
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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