Hydrochloric Acid → HCID 86730361, compound

Temperature

0 °C

Commercially available 3,4-dihydroxybenzaldehyde (6.5 g, 47.1 mmol) and potassium carbonate (6.83 g, 49.4 mmol) were suspended in N,N-dimethylformamide (30 mL), then 3-fluoropropyl 4-methylbenzenesulfonate described in Production Example 5-1 (11.3 g, 48.4 mmol) was added under nitrogen atmosphere at loom temperature, and the mixture was stirred for 37 hours. The mixture was cooled to 0° C. and then 2 M hydrochloric acid, ethyl acetate, and water were added for partition. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then filtered. The solvent was evaporated and the resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=4:1-2:1-1:1). The target fraction was concentrated under vacuum to obtain the title compound (4.62 g, 50%).

1. additionwas added under nitrogen atmosphere at loom temperature
2. customfor partition
3. washThe organic layer was washed with water
4. dry with materiala saturated saline solution, dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customThe solvent was evaporated
7. customthe resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=4:1-2:1-1:1)
8. concentrationThe target fraction was concentrated under vacuum

ORD record

ord-3c62ffa955be4fa1bd8a9972fdb2ac90

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933099B2