(Trifluoromethyl)trimethylsilane → 1-Fluoro-2-(trifluoromethylsulfonyl)benzene

The solution of EXAMPLE 12 (44.3 g) in a solution of 450 ml was added to a round bottomed flask fitted with overhead stirrer, nitrogen inlet, cold-water bath and temperature probe. It was cooled down to 12° C. (((CH3)2N)3S)+(F2Si(CH3)3)−, also known as TASF (6.1 g), was added in one portion. Ruppert's reagent (370 g, CH3SiCF3) was charged slowly to the reaction mixture while maintaining the internal temperature less than 23° C. The reaction was completed after addition. Water (220 g) was added to quench the reaction, the layers were separated, and the organic layer was washed twice with 220 g of water. The organic solution was distilled under vacuum with the bath temperature at 50° C. Heptanes (500 g) were added to the residue, and the mixture was distilled down until the solvent was removed. 1H NMR (400 MHz, CDCl3) δ 8.01-8.05 (m, 1H), 7.84-7.87 (m, 1H), 7.44-7.48 (m, 1H), 7.36-7.39 (m 1H).

1. customfitted with overhead stirrer, nitrogen inlet
2. additionwas added in one portion
3. temperaturewhile maintaining the internal temperature less than 23° C
4. additionafter addition
5. customto quench
6. customthe reaction
7. customthe layers were separated
8. washthe organic layer was washed twice with 220 g of water
9. distillationThe organic solution was distilled under vacuum with the bath temperature at 50° C
10. additionHeptanes (500 g) were added to the residue
11. distillationthe mixture was distilled down until the solvent
12. customwas removed

ORD record

ord-f258a20a2fb84ce681e031dde36193e4

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08168784B2