Compound 1m

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Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

2.0 M LDA in THF (5.5 mL, 11 mmol) was diluted with THF (25 mL) and cooled to -78 °C. To this solution was added 4-bromo-1-chloro-2- fluorobenzene (S13, 10 mmol) dropwise at same temperature. After stirring for 1 h, DMF (1.0 mL, 13 mmol) was added dropwise, and the reaction mixture was warmed to room temperature overnight. The reaction mixture was quenched with dropwise addition of 0.1 M HCl (aq), and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over Na₂SO₄, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography to afford 6-bromo-3-chloro-2-fluorobenzaldehyde (S15). 1m was prepared from S15 following the same procedure as the synthesis of 1f. ¹H NMR (600 MHz, CDCl₃): δ 10.51 (s, 1H), 7.52 (dd, J = 8.3, 7.6 Hz, 1H), 7.03 (d, J = 7.6 Hz, 1H), 3.00 (q, J = 7.5 Hz, 2H), 1.21 (t, J = 7.5 Hz, 3H). ¹³C NMR (150 MHz, CDCl₃): δ 188.21 (d, J = 11.1 Hz), 161.33 (d, J = 259.6 Hz), 147.07, 135.25 (d, J = 1.6 Hz), 126.34 (d, J = 4.7 Hz), 123.14 (d, J = 5.4 Hz), 119.14 (d, J = 18.1 Hz), 26.43, 15.29. ¹⁹F NMR (376 MHz, CDCl₃): δ -123.46. HRMS (ESI-TOF): m/z calculated for C₉H₉ClFO⁺ [M+H]⁺ 187.0320, found 187.0323.