Acetic Acid → HCID 11637634, compound

Temperature

110 °C

To a solution of 2′-hydroxyacetophenone (0.68 g, 5 mmol) in 10 mL anhydrous pyridine was added 3,5-difluoro-4-methoxybenzoyl chloride (1.03 g, 5 mmol) and the reaction mixture was stirred at rt for 15 h under nitrogen atmosphere. The reaction mixture was poured into 100 mL 2N HCl. The solid was filtered off, washed with water and dried under vacuum to give a white solid (1.44 g, 94%). The compound (1.42 g, 4.63 mmol) was dissolved in 10 mL anhydrous pyridine. Powdered KOH (0.78 g, 13.9 mmol) was added and the reaction mixture was stirred at rt overnight under nitrogen. Water (50 mL) was added and the solid was isolated by filtration, and washed with water to give yellow solid (1.05 g, 74%). To a suspension of the yellow solid (0.82 g, 2.67 mmol) in 6 mL glacial AcOH was added 3 drops of conc. HCl and the reaction mixture was stirred at 110° C. for 2 h. The mixture was cooled to rt and 50 mL water was added. The solid was isolated by filtration, washed with water and dried under vacuum to give 2-(3,5-difluoro-4-methoxyphenyl)chromen-4-one as a white solid (0.61 g, 79%). 2-(3,5-Difluoro-4-methoxyphenyl)chromen-4-one was suspended in 15 mL hydroiodic acid. Glacial AcOH (6 mL) was added and the reaction mixture was stirred at 110° C. for 4 h. The mixture was cooled to rt. Water (100 mL) was added and the solid was isolated by filtration, washed with water and dried under vacuum. The crude compound was washed with 1:1 dichloromethane and MeOH (15 mL) to give 2-(3,5-difluoro-4-hydroxyphenyl)-4H-chromen-4-one (0.416 g, 73%) as a pale yellow solid. MS (ES) m/z: 275.04 (M+1); Mp. 275-276° C.

1. temperatureThe mixture was cooled to rt
2. customthe solid was isolated by filtration
3. washwashed with water
4. customdried under vacuum
5. washThe crude compound was washed with 1:1 dichloromethane and MeOH (15 mL)

ORD record

ord-914e637f44ab4593a26fabcf8d1cbb36

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242130B2