Nitric Acid → 1-Bromo-2,4-difluoro-5-nitrobenzene

Temperature

0 °C

To a 0° C. mixture of 1-bromo-2,4-difluorobenzene (20.0 g, 11.7 mL, 0.100 mol) and H2SO4 (76.8 mL) was added HNO3 (68.0 mL) over 45 min at such a rate that the internal temperature was <7° C. The resulting mixture was stirred for 1 h at 0° C., poured into ice water (400 mL), stirred vigorously for 2-3 min and extracted with CH2Cl2 (400 mL). The organic layers were washed with brine (1×500 mL), dried over Na2SO4, filtered and evaporated to give the product as a yellow oil (23.5 g, 95% yield). 1H NMR (CDCl3) δ 8.39 (t, J=7.2 Hz, 1H), 7.14 (ddd, J=0.3, 7.8, 9.9 Hz, 1H).

1. customwas <7° C
2. stirringstirred vigorously for 2-3 min
3. extractionextracted with CH2Cl2 (400 mL)
4. washThe organic layers were washed with brine (1×500 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customevaporated

ORD record

ord-72a409bc390f488db36491a6c1b882ed

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07446204B2