2-(Bromomethyl)-1,3-difluorobenzene → HCID 21702642, compound

To a solution of 5-bromo-3-hydroxy-2(1H)-pyridinone (U.S. Pat. No. 3,471,506, 10.0 g, 52.6 mmol) in dioxane (30 mL) and H2O (15 mL) was added NaOH (2.1 g, 52.5 mol) dissolved in H2O (12.5 mL). To this mixture is added di-t-butyl-dicarbonate (12.5 g, 57.5 mmol), and the mixture is stirred at room temperature for 6 hours. At this time, the mixture is filtered, and the solid is washed with H2O (50 mL), and is dissolved in CH2Cl2 (100 mL). This organic solution is washed with brine, dried over MgSO4, and concentrated to yield 5-bromo-3-(t-butoxycarbonyloxy)-2(1H)pyridinone. A solution of 5-bromo-3-(t-butoxycarbonyloxy)-2(1H)-pyridinone (5.0 g, 17.2 mmol), AG2CO3 (4.74 g, 17.2 mmol) and α-bromo-2,6-difluorotoluene (3.56 g, 17.2 mmol) in toluene (60 mL) is heated to 42° for 24 hours in the dark. At this time the mixtut is filtered. The filtrate is concentrated in vacuo, and the residue is dissolved in EtOAc (150 mL) and washed with H2O (50 mL) and brine (50 mL), dried over MgSO4 and concentrates in vacuo. Chromatography (silica, 9:1 EtOAc/hexane) yields 5-bromo-3-(t-butoxycarbonyloxy)-2-(2,6-difluorobenzyloxy)-pyridine.

1. filtrationAt this time the mixtut is filtered
2. concentrationThe filtrate is concentrated in vacuo
3. dissolutionthe residue is dissolved in EtOAc (150 mL)
4. washwashed with H2O (50 mL) and brine (50 mL)
5. dry with materialdried over MgSO4 and concentrates in vacuo

ORD record

ord-e5dec4ee8592454a9d43942e30d6e987

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06291530B1