[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]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.
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