Trifluoroacetic anhydride → HCID 619795, compound

2-Fluoro-5-nitroaniline (7.0 g, 45 mmol) was dissolved in CH2 Cl2 (200 mL) and Et3 N (7.0 mL, 49 mmol) was added. Then (CF3 CO)2O (7.5 mL, 11.3 g, 54 mmol) in 25 mL of CH2 Cl2 was added dropwise at 0° C., and the mixture was stirred for 24 h at room temperature. The reaction mixture was washed with water (3×300 mL) and saturated aq. NaHCO3 (300 mL). The organic layer was separated, and an aqueous layer was extracted with CH2 Cl2 (2×100 mL). Combined organic solutions were dried over Na2 SO4, evaporated, and the title compound was isolated as a light beige solid with m.p. 112-113° C.; yield—10.5 g (93%). 1H NMR (CDCl3, 300 MHz, ppm): δ=7.35 (t, JHH=3JHF=9.2, 1H, H-3), 8.14 (ddd, 4JHH=2.8, 4JHF=4.2, 3JHH=9.2, 1H, H-4), 8.22 (br s, NH), 9.18 (dd, 3JHH=2.9, 4JHF=6.4, 1H, H-6); 13C NMR (CDCl3, 75.5 MHz, ppm): δ=115.1 (q, 1JCF=289, CF3), 116.1 (d, 2JCF=22, C-3), 117.8 (d, 3JCF=2.3, C-4/6), 122.3 (d, 3JCF=9.5, C-6/4), 124.6 (d, 2JCF=12.7, C-1), 144.5 (C-5), 154.4 (q, 2JCF=42, CO), 155.8 (d, 1JCF=256, C-2); EI-MS: m/z (rel. int., %)=223 (100) [M—HCO]+, 154 (21), 126 (18), 99 (17).

1. additionEt3 N (7.0 mL, 49 mmol) was added
2. washThe reaction mixture was washed with water (3×300 mL) and saturated aq. NaHCO3 (300 mL)
3. customThe organic layer was separated
4. extractionan aqueous layer was extracted with CH2 Cl2 (2×100 mL)
5. customCombined organic solutions were dried over Na2 SO4
6. customevaporated

ORD record

ord-6abd8e20c63c4e81b47936a4351c8bf3

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735444B2