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

HRID 1255246Notes

Reaction equation

HRID 1255246 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

Sources & evidence

ORD record
ord-52192d3d996d475fbcdf5a12cf26c473
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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