Phosphorus oxybromide → HCID 22595770, compound

Alternatively, the above reaction can be run using the following procedure: POBr3 (39.2 g, 137 mmol, 2 equiv) was added to a stirred solution of 3 (20 g, 68 mmol) in dichloroethane (150 mL). The reaction was heated to reflux for 8 h. After cooling to rt, the reaction was quenched by the slow addition of ice. (Here I let it stir over the weekend—but not necessary). The organic layer was separated and the aqueous layer was extracted with CHCl3 (2×100 mL). The combined organic layer was washed with NaHCO3 (1×150 mL), H2O (1×150 mL), NaHSO3 (1×150 mL), H2O (1×150 mL), brine (1×150 mL) and dried over MgSO4. The residue was recrystallized from EtOH to afford the desired product, 16.12 g (67%). An additional 1.87 g was obtained by column chromatography of the concentrated filtrate (SiO2, 5% ethyl acetate-hexane). Total yield 17.99 g (74%).

1. customAlternatively, the above reaction
2. temperatureThe reaction was heated
3. temperatureto reflux for 8 h
4. customthe reaction was quenched by the slow addition of ice
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with CHCl3 (2×100 mL)
7. washThe combined organic layer was washed with NaHCO3 (1×150 mL), H2O (1×150 mL), NaHSO3 (1×150 mL), H2O (1×150 mL), brine (1×150 mL)
8. dry with materialdried over MgSO4
9. customThe residue was recrystallized from EtOH

ORD record

ord-ddb4d4b88a7a441aa2bf910ad57ebdf6

Source dataset

uspto-grants-2005_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06844340B2