Nitric Acid → HCID 67119669, compound

3,4,5-Trifluorophenol (14.81 g, 0.1 mol) was dissolved in glacial acetic acid (50 mL) and cooled to 4° C. while concentrated nitric acid (5 mL, 70%) was added dropwise over 15 min, during which time the color of the mixture becomes yellow. Upon complete addition of HNO3, the reaction mixture was allowed to warm to room temperature and stirred for an additional 30 min. TLC analysis of an aliquot extracted into ethyl acetate indicates that a new non-polar spot was formed and the complete consumption of starting material. The mixture was then diluted with ethyl acetate (200 mL), transferred to separatory funnel, and washed copiously with water (3×100 mL). The organic layer was finally washed with brine, dried over anhyd MgSO4, and evaporated under reduced pressure to afford crude product as a yellowish oil. (17.3 g, 90%). This crude material was used directly in the subsequent reaction described in Intermediate 6. 1H NMR (400 MHz, CDCl3): 6.84 (m, 1H, ArH), 10.28 (brs, 1H, OH).

1. additionwas added dropwise over 15 min, during which time the color of the mixture
2. extractionTLC analysis of an aliquot extracted into ethyl acetate
3. customwas formed
4. customthe complete consumption of starting material
5. additionThe mixture was then diluted with ethyl acetate (200 mL)
6. customtransferred to separatory funnel
7. washwashed copiously with water (3×100 mL)
8. washThe organic layer was finally washed with brine
9. dry with materialdried over anhyd MgSO4
10. customevaporated under reduced pressure
11. customto afford crude product as a yellowish oil

ORD record

ord-8f64bd218f2f4b4a9c96aef436de39d7

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034861B2