Dimethylformamide → Tert-butyl 2-formyl-6-(trifluoromethyl)phenylcarbamate

Temperature

-78 °C

To a solution of tert-butyl 2-(trifluoromethyl)phenylcarbamate (1.0 g, 3.83 mmol) and N,N,N′N′-tetramethylethylenediamine (1.27 mL, 8.43 mmol) in 20 mL of anhydrous THF at −78° C. was added sec-butyllithium (8.43 mL of a 1.0 M solution in hexanes, 8.43 mmol) dropwise over 15 min. The reaction was stirred at −78° C. for 1 h and then there was added DMF (0.33 mL, 4.21 mmol). The reaction was stirred at −78° C. for 1 h and then was quenched with sat'd aq NH4Cl (10 mL) and allowed to warm to ambient temperature. The reaction mixture was diluted with water and extracted with EtOAc. The organics were washed with 1N HCl and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography (230-400 mesh silica gel, elution with 6:1 hexane/EtOAc) to afford 0.4 g (36%) of the title compound. 1H NMR (CDCl3): δ 10.06 (s, 1H), 8.07 (d, 1H, J=7.7 Hz), 7.83 (d, 1H, J=7.8 Hz), 7.43 (t, 1H, J=7.8 Hz), 6.83 (broad s, 1H), 1.47 (s, 9H). LRMS (ESI): 290.15 (M+H)+.

1. stirringThe reaction was stirred at −78° C. for 1 h
2. customwas quenched with sat'd aq NH4Cl (10 mL)
3. temperatureto warm to ambient temperature
4. additionThe reaction mixture was diluted with water
5. extractionextracted with EtOAc
6. washThe organics were washed with 1N HCl and brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography (230-400 mesh silica gel, elution with 6:1 hexane/EtOAc)

ORD record

ord-3730381d6fd74e82a58ebb1421c5b2e0

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07618980B2