Phosphorus oxybromide → HCID 22595770, compound

Temperature

100 °C

A mixture of 3 (4.71 g, 16.1 mmol) and POBr3 (9.23 g, 32.2 mmol) were heated to 100° C. After 2 h, the reaction was cooled to rt and partitioned between EtOAc and H2O, adding ice when necessary. The mixture was stirred overnight to break up the solid materials. Et2O (100 mL) was added and the organic phase was removed. The remaining aqueous phase was extracted with EtOAc (3×100 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated to afford 5.5 g (96%) of the desired product which was used without further purification. An analytically pure sample was obtained by recrystallization (EtOH) to provide a fluffy off-white solid, mp 120° C. Rf 0.61 (10% Ethyl acetate-hexane). 1H NMR (CDCl3, 300 MHz) δ 8.16 (d, J=9.1 Hz, 1H), 8.16 (m, 1H), 7.92 (dd, J=2.2, 9.1 Hz, 1H); 19F NMR (CDCl3, 300 MHz) δ −57.63; 13C NMR (CDCl3, 75 MHz) δ 146.50, 137.35, 134.25, 131.88, 131.32, 124.45, 124.40, 122.44, 121.96, 118.76; IR (KBr) υmax 1606, 1588, 1552, 1492, 1426, 1382, 1361, 1308, 1283, 1219, 1180, 1169, 1157, 1134, 1097, 1023, 960, 846, 823, 792, 693, 661, 632 cm−1.

1. temperaturethe reaction was cooled to rt
2. custompartitioned between EtOAc and H2O
3. additionadding ice when necessary
4. additionEt2O (100 mL) was added
5. customthe organic phase was removed
6. extractionThe remaining aqueous phase was extracted with EtOAc (3×100 mL)
7. washThe combined organic phases were washed with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated

ORD record

ord-b6f5dab156f64a2ab505738684a19680

Source dataset

uspto-grants-2005_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06844340B2