Hydrochloric Acid → 3-Chloro-4-(cyanomethyl)benzoyl chloride

HRID 7739Notes

Reaction equation

HRID 7739 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[Cl:12].[C-:13]#[N:14].[Na+].[ClH:16]>CN(C=O)C.O>[Cl:12][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:3]=1[CH2:2][C:13]#[N:14])[C:7]([Cl:16])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 219249954-(Bromomethyl)-3-chlorobenzoic acid

Product 1

HCID 219909693-Chloro-4-(cyanomethyl)benzoyl chloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 4-(bromomethyl)-3-chlorobenzoic acid (4.0 g, 16 mmol) in DMF (120 mL) and H2O (40 mL) was treated with NaCN (2.4 g, 49 mmol) and heated to 80° C. for 2 h. The mixture was cooled to rt and acidified with 1N HCl. The aqueous mixture was extracted with CH2Cl2 (3×25 mL). The combined organic layers were concentrated under reduced pressure and dissolved in MTBE. The organic mixture was washed with H2O and brine (3×25 mL), dried over MgSO4, filtered and concentrated to afford 3-chloro-4-(cyanomethyl)benzoyl chloride.

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionThe aqueous mixture was extracted with CH2Cl2 (3×25 mL)
  3. concentrationThe combined organic layers were concentrated under reduced pressure
  4. dissolutiondissolved in MTBE
  5. washThe organic mixture was washed with H2O and brine (3×25 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-768846e0a8dc4bde93680feebe296211
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Reaction notes

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