Hydrochloric Acid → 5-(Difluoromethoxy)picolinic acid

To a solution of methyl 5-(difluoromethoxy)picolinate (0.750 g, 3.69 mmol) in 1,4-dioxane (18.46 ml) was added sodium hydroxide, 1N aqueous solution (7.4 ml, 7.4 mmol) and the reaction mixture was stirred at RT for overnight. Then hydrogen chloride, 4.0M solution in 1,4-dioxane (1.8 ml, 7.38 mmol) was added and stirred for 1 h. The reaction mixture was concentrated and was diluted with water and extracted with EtOAc. The organic extract was dried over MgSO4, filtered and concentrated to give 5-(difluoromethoxy)picolinic acid (0.6013 g, 3.18 mmol, 86% yield). MS m/z: 190.2 [M+H].

1. stirringstirred for 1 h
2. concentrationThe reaction mixture was concentrated
3. additionwas diluted with water
4. extractionextracted with EtOAc
5. extractionThe organic extract
6. dry with materialwas dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-c96a12ecde034729a6323e6ef988d9df

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309263B2