1-(Bromomethyl)-2,4-difluorobenzene → HCID 178490654, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 2A (0.3 g, 0.8 mmol) in N,N-dimethylformamide/tetrahydrofuran (1:4, 10 mL) were added potassium t-butoxide (0.11 g, 1.0 mmol) and 1-(bromomethyl)-2,4-difluorobenzene (Aldrich) (0.21 g, 1.0 mmol). The reaction was stirred at 80° C. overnight and then diluted with ethyl acetate (10 mL). The mixture was washed with 1M NaHCO3 and this aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using an Analogix® IT280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford 20 mg (5%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.47 (s, 6H) 1.52 (s, 6H) 3.72 (s, 3H) 5.35 (s, 2H) 7.07 (d, 3H) 7.32 (d, 1H) 7.37 (d, J=2.71 Hz, 1H) 7.40-7.50 (m, J=8.81 Hz, 1H); MS (ESI+) m/z 493 (M+H)+.

Provenance & Evidence