Dimethylformamide → HCID 86651255, compound

Temperature

-78 °C

To a solution of (4-bromo-3-methyl-phenyl)-carbamic acid ethyl ester (210 mg) in THF (4 mL) was added n-BuLi (0.71 mL, 2.5 M solution in hexane) at −78° C. The mixture was stirred at −78° C. for 40 min, then DMF (0.31 mL) was added. The mixture was stirred at −78° C. for 40 min and then warmed up to room temperature. The reaction mixture was quenched with saturated NH4Cl aqueous solution (11 mL) and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, EtOAc:Hexane=5:95 to 40:60) to give (4-formyl-3-methyl-phenyl)-carbamic acid ethyl ester: MS (ESI): m/z 206 (M+1); 1H NMR (CDCl3, 400 MHz) δ 10.14 (s, 1H), 7.75 (d, 1H), 7.39 (dd, 1H), 7.32 (s, 1H), 6.92 (s, 1H), 4.25 (q, 2H), 2.65 (s, 3H), 1.32 (t, 3H).

1. stirringThe mixture was stirred at −78° C. for 40 min
2. temperaturewarmed up to room temperature
3. customThe reaction mixture was quenched with saturated NH4Cl aqueous solution (11 mL)
4. extractionextracted with EtOAc
5. washThe organic extracts were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude product was purified by column chromatography (SiO2, EtOAc:Hexane=5:95 to 40:60)

ORD record

ord-82dd05d501144b369cf088afd3412973

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222248B2