Sulfuric Acid → 3-Acetoxy-2-(2-chloro-5-(difluoromethoxy)phenyl)propanenitrile

HRID 1437610Notes

Reaction equation

HRID 1437610 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([F:11])[F:10])=[CH:4][C:3]=1[CH:12]([CH2:15][OH:16])[C:13]#[N:14].C(#N)C.[C:20](OC(=O)C)(=[O:22])[CH3:21].OS(O)(=O)=O>O>[C:20]([O:16][CH2:15][CH:12]([C:3]1[CH:4]=[C:5]([O:8][CH:9]([F:11])[F:10])[CH:6]=[CH:7][C:2]=1[Cl:1])[C:13]#[N:14])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 7918Acetic AnhydrideHCID 669058862-Chloro-5-(difluoromethoxy)phenyl-3-hydroxypropanenitrile

Product 1

HCID 249912273-Acetoxy-2-(2-chloro-5-(difluoromethoxy)phenyl)propanenitrileYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 5 mL screw-capped test tube was charged with 250 mg (1.00 mmol) of 2-(2-chloro-5-(difluoromethoxy)phenyl)-3-hydroxypropanenitrile, 0.4 mL of acetonitrile and 122 μL (1.3 mmol) of acetic anhydride. This mixture was stirred briefly with a melting point capillary having the tip wetted with conc. H2SO4 to give an immediate exotherm. After 15 minutes the mixture was diluted with water and extracted with butyl chloride. The extract was washed with water 3 times, dried (Na2SO4), and stripped of solvent under high vacuum to give 233 mg (96%) of the desired ester product, i.e., 3-acetoxy-2-(2-chloro-5-(difluoromethoxy)phenyl)propanenitrile, as a colorless oil.

Workup

  1. customA 5 mL screw-capped test tube
  2. customto give an immediate exotherm
  3. extractionextracted with butyl chloride
  4. washThe extract was washed with water 3 times
  5. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-026a99be8173434c94919aba8f21b799
Source dataset
uspto-grants-2009_11
Patent number
US07622504B2

Reaction notes

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