Triethylamine → HCID 11045242, compound

Temperature

0 °C

To a round-bottomed flask (100 mL) equipped with magnetic stir bar and addition funnel (10 mL) was charged 1b (3.0 g, 16.5 mmol), CH2Cl2 (50 mL) and triethylamine (3.3 g, 33 mmol, 2 equiv). The mixture was cooled to 0° C. in an ice bath. The funnel was charged with Tf2O (6.9 g, 4.18 mL, 24.8 mmol, 1.5 equiv) which was added dropwise over 1 h. After several hours at 0° C., the mixture was allowed to warm up to room temperature and washed with H2O. The organic phase was washed with brine (25 mL), separated and dried over anhydrous MgSO4. The organic phase was treated with decolorizing charcoal, filtered and evaporated under reduced pressure. Compound 2b was obtained as colorless crystals by recrystallization from hexanes (4.5 g, 87%), mp. 105-107° C., lit.21 108-110° C. 1H NMR (CDCl3): δ 9.95 (s, 1H), 7.17 (s, 2H), 3.99 (s, 6H); 13C NMR (CDCl3): δ 190.65, 153.45, 136.13, 132.25, 118.85 (q, 1JCF=321.2 Hz), 106.15, 56.89; 19F {13C} NMR (CDCl3): δ −74.08. Anal. Calcd for C10H9F3O6S: C, 38.22; H, 2.89. Found: C, 38.43; H, 2.89.

1. customTo a round-bottomed flask (100 mL) equipped with magnetic stir bar and addition funnel (10 mL)
2. additionwas added dropwise over 1 h
3. waitAfter several hours at 0° C.
4. temperatureto warm up to room temperature
5. washwashed with H2O
6. washThe organic phase was washed with brine (25 mL)
7. customseparated
8. dry with materialdried over anhydrous MgSO4
9. additionThe organic phase was treated with decolorizing charcoal
10. filtrationfiltered
11. customevaporated under reduced pressure

ORD record

ord-d104569a48bc4e6bb14c1428cb79f5cb

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921614B1