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

HRID 1690836Notes

Reaction equation

HRID 1690836 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-3014f03bbca94aafa505af2a58f7c6fc
Source dataset
uspto-grants-2012_04
Patent number
US08153688B2

Reaction notes

Loading…