alpha,alpha,alpha-Trifluoro-3-nitro-o-xylene → HCID 11198316, compound

Temperature

2.5 °C

To H2SO4 (110 mL, 96%) stirring under a nitrogen atmosphere at 0-5° C. was added N-iodosuccinimide (41.13 g, 1.5 eq). The resulting black/dark red mixture was stirred at 0-5° C. for 40 minutes. To this was added dropwise commercially available 2-methyl-3-nitrobenzotrifluoride (25.0 g, 121.9 mmol) in H2SO4 (75 mL). Once the addition was completed, ca. 1 hour, the mixture was stirred at 5-10° C. for 5 hours. The resulting mixture was poured into ice (600 mL) and extracted with EtOAc (400 mL, 3×200 mL). The extracts were combined, washed with saturated aqueous Na2SO3 (500 mL) and H2O (400 mL). The organic phase was then dried (anhydrous MgSO4). After filtration the solvent was removed in vacuo to give a dark oil. Purification was carried out by column chromatography (silica gel, eluting hexane) to give the title compound as a light yellow/green oil which solidified on standing (34.81 g, 86%).

1. additionOnce the addition
2. waitwas completed, ca. 1 hour
3. stirringthe mixture was stirred at 5-10° C. for 5 hours
4. extractionextracted with EtOAc (400 mL, 3×200 mL)
5. washwashed with saturated aqueous Na2SO3 (500 mL) and H2O (400 mL)
6. dry with materialThe organic phase was then dried (anhydrous MgSO4)
7. filtrationAfter filtration the solvent
8. customwas removed in vacuo
9. customto give a dark oil
10. customPurification
11. washwas carried out by column chromatography (silica gel, eluting hexane)

ORD record

ord-37ec67d5151f47639f0325806f8ff041

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06576656B1