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

HRID 446370Notes

Reaction equation

HRID 446370 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+].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]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 768Hydrogen CyanideHCID 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 [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.

Workup

  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

Sources & evidence

ORD record
ord-12c57a74242848ebba9cc1364ce769e6
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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