4-Toluenesulfonyl chloride → HCID 68679977, compound

To a solution of 4-amino-3-bromobenzotrifluoride (20.0 g, 83.3 mmol) in pyridine at room temperature is added p-toluenesulfonyl chloride (19.8 g, 104.1 mmol) in portions over 3 minutes, and the resulting mixture stirred for 52 hours. The suspension is poured into an ice-water mix (300 ml), filtered; and the filtered solid is washed with water (250 ml). The solid is dissolved in dichloromethane (200 ml) and the resulting solution is washed with 1N HCl (2×150 ml), water (2×200 ml), dried (Na2SO4), and concentrated to a solid. The solid is suspended in ethanol (700 ml) and heated at reflux for 10 minutes, filtered while hot to remove insolubles, and the filtered solids washed with ethanol (250 ml). After concentration of the filtrate, the resulting solid is suspended in methanol (500 ml), treated with K2CO3 (2.0 g, 14.4 mmol), and the mixture is stirred at room temperature for 46 hours. After filtration of the suspension, the filtered solid is washed with methanol (150 ml), and the filtrate is concentrated to give the title compound as a foam. Mass spectrum (ES+): 394 (M+).

1. additionmix (300 ml)
2. filtrationfiltered
3. washand the filtered solid is washed with water (250 ml)
4. dissolutionThe solid is dissolved in dichloromethane (200 ml)
5. washthe resulting solution is washed with 1N HCl (2×150 ml), water (2×200 ml)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated to a solid
8. temperatureheated
9. temperatureat reflux for 10 minutes
10. filtrationfiltered while hot
11. customto remove insolubles
12. washthe filtered solids washed with ethanol (250 ml)
13. stirringthe mixture is stirred at room temperature for 46 hours
14. filtrationAfter filtration of the suspension
15. washthe filtered solid is washed with methanol (150 ml)
16. concentrationthe filtrate is concentrated

ORD record

ord-dccd6a86ce7348689287cf0654438d8b

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07749992B2