Triethylamine → Benzoic acid, 5-ethyl-2-[[(trifluoromethyl)sulfonyl]oxy]-, methyl ester

To 3.0 g (16.6 mmol) of methyl 5-ethyl-2-hydroxybenzoate in 100 mL of CH2Cl2 at 0° C was added 5.8 mL (41.5 mmol, 2.5 eq.) of Et3N. To this stirred solution was added dropwise 3.6 mL (21.6 mmol, 1.3 eq.) of Tf2O. Following complete addition 0.2 g (cat.) of 4-dimethylamino pyridine was added and the reaction mixture was allowed to warm to room temperature. After 4 h stirring at this temperature the reaction was judged complete, and quenched by the addition of a saturated aqueous solution of NaHCO3 (100 mL). The resulting layers were separated and the aqueous layer extracted twice with CH2Cl2 (100 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue, was purified by column chromatography to yield the desired methyl 5-ethyl-2-{[(trifluoromethyl)sulfonyl]oxy}benzoate. 1H NMR (400 MHz, CDCl3): δ=7.94 (d, J=2.3 Hz, 1 H), 7.47 (dd, J=2.3, 8.4 Hz, 1 H), 7.24 (d, J=8.4 Hz, 1 H), 4.00 (s, 3 H), 2.76 (q, J=7.6 Hz, 2 H), 1.28 (t, J=7.6 Hz, 3 H).

1. additionwas added
2. customquenched by the addition of a saturated aqueous solution of NaHCO3 (100 mL)
3. customThe resulting layers were separated
4. extractionthe aqueous layer extracted twice with CH2Cl2 (100 mL)
5. dry with materialThe combined organic layers were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe resulting residue, was purified by column chromatography

ORD record

ord-c05828f6d53c4bc48d7bf6e98b60cbc6

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544717B2