Potassium Cyanide → 2-Chloro-5-(cyanomethyl)benzoic acid

HRID 446363Notes

Reaction equation

HRID 446363 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9].[C-:13]#[N:14].[K+]>CN(C=O)C.O>[Cl:12][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][C:13]#[N:14])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 219000095-(Bromomethyl)-2-chlorobenzoic acid

Product 1

HCID 581685272-Chloro-5-(cyanomethyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(bromomethyl)-2-chlorobenzoic acid [WO 2001044170] (1.75 g) in DMF (20 mL) was treated with a solution of potassium cyanide (0.91 g) in water (7 mL) and the resulting solution was stirred at room temperature over 3 days. 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 (5 mL), venting any liberated HCN through bleach solution via a stream of nitrogen. After being stirred for 20 minutes, 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 brown solid. Yield 1.25 g.

Workup

  1. extractionextracted twice with ethyl acetate
  2. stirringAfter being stirred for 20 minutes
  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-deed51252e7749d791f7e7f926a027f1
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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