Nitric Acid → 757251-37-9

Temperature

15 °C

A solution of 2-chloro-6-fluorophenol (1.0 g, 6.82 mmol) in concentrated acetic acid (3.0 mL) was cooled to 0° C. Fuming nitric acid (559 mg, 8.87 mmol) was added dropwise, maintaining the reaction temperature between 10 to 20° C. The reaction was allowed to stir at 0° C. for 3 h. The mixture was poured over ice and was allowed to warm to room temperature. The aqueous was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (1×50 mL), dried over Na2SO4, and evaporated under reduced pressure. The crude red solid was purified using the Biotage Quad 4 (25 M column) eluting with 9:1 Hexanes/EtOAc to afford the title compound as a yellow solid (326 mg, 1.70 mmol; 25% yield). 1H-NMR (DMSO-d6) δ 11.74 to 12.77 (broad s, 1H), 8.10 to 8.16 (m, 2H).

1. additionThe mixture was poured over ice
2. temperatureto warm to room temperature
3. extractionThe aqueous was extracted with EtOAc (3×50 mL)
4. washThe combined organic layers were washed with brine (1×50 mL)
5. dry with materialdried over Na2SO4
6. customevaporated under reduced pressure
7. customThe crude red solid was purified
8. washeluting with 9:1 Hexanes/EtOAc

ORD record

ord-8260f27c95db4a77951c0ab7c7b681bf

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076488B2