2-chloro-3-nitro-5-(trifluoromethyl)benzoic acid

Preparation of 2-chloro-3-nitro-5-trifluoromethylbenzoic acid [Show Image]2-Chloro-5-trifluoromethylbenzoic acid (6.5044 g, 28.965 mmol) was added to a solution of sulfuric acid (23 mL) and fuming nitric acid (3.2 mL), with an overhead stirring. The mixture was warmed to 90°C over 26 min then a further 10 mL of sulfuric acid was added to the thick mixture and stirring was continued. After 45 min at 90°C the mixture was cooled to ambient temperature and poured into crushed ice (150 g), rinsing forward with icy water (50 mL). The product was isolated by vacuum filtration, washed with cold water, and dried in vacuo to give 7.3752 g (94.7 percent). LCMS: R2-Chloro-5-trifluoromethylbenzoic acid (6.5044 g, 28.965 mmol) was added to a solution of sulfuric acid (23 mL) and fuming nitric acid (3.2 mL), with an overhead stirring. The mixture was warmed to 90°C over 26 min then a further 10 mL of sulfuric acid was added to the thick mixture and stirring was continued. After 45 min at 90°C the mixture was cooled to ambient temperature and poured into crushed ice (150 g), rinsing forward with icy water (50 mL). The product was isolated by vacuum filtration, washed with cold water, and dried in vacuo to give 7.3752 g (94.7 percent). LCMS: R2-Chloro-5-trifluoromethylbenzoic acid (6.5044 g, 28.965 mmol) was added to a solution of sulfuric acid (23 mL) and fuming nitric acid (3.2 mL) , with an overhead stirring. The mixture was warmed to 90 °C over 26 min, then a further 10 mL of sulfuric acid was added to the thick . mixture and stirring was continued. After 45 min at 90 °C the mixture was cooled to ambient temperature and poured into crushed ice (150 g) , rinsing forward with icy water (50 mL) . The product was isolated by vacuum filtration, washed with cold water, and dried in vacuo to give 7.3752 g (94.7 percent) . LCMS: R2-chloro-5-trifluoromethylbenzoic acid (8.98 g, 40 mmol) was dissolved in 14.4 mL of concentrated sulfuric acid. Stir until completely dissolved, to the reaction solution, fuming sulfuric acid (50percent) 9.6 mL was added. cool in ice bath to 0 ° C, Slowly add 7.0 mL of fuming nitric acid to the reaction system. Keeping the temperature of the reaction system below 60 ° C during the dropwise addition, After 30 minutes, After stirring for 1 hour, Add ice water 150mL, Precipitated in white, Filtration, washing with water and drying to give the intermediate 2-chloro-3-nitro-5-(trifluoromethyl)benzoic acid 1a. The white solid was 8.73 g, yield 81.1percent.

Molecular Weight:269.56
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:1
Exact Mass:268.9702698
Monoisotopic Mass:268.9702698
Topological Polar Surface Area:83.1
Heavy Atom Count:17
Complexity:330
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes