Sodium Iodide → 3-Fluoro-2-((trimethylsilyl)methoxy)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-fluoro-2-hydroxybenzaldehyde (4.18 g, 29.8 mmol) and K2CO3 (12.25 g, 89 mmol) in DMF (81 mL) was added (chloromethyl)trimethylsilane (4.06 g, 33.1 mmol) and NaI (4.96 g, 33.1 mmol). Upon completion of addition, the mixture was heated in 65° C. oil bath overnight. After this time, the mixture was cooled to rt, quenched with water (20 mL) and then extracted with Et2O (2×30 mL). The combined organic layers were washed with H2O (2×15 mL), dried (Na2SO4), filtered and concentrated to afford Compound 1A as a light yellow oil (6.7 g, 98% yield). 1H NMR (500 MHz, CDCl3) δ ppm 10.41 (s, 1 H), 7.60 (dd, J=9.1, 1.7 Hz, 1 H), 7.32 (ddd, J=11.8, 8.3, 1.7 Hz, 1 H), 7.01-7.12 (m, 1 H,) 4.01 (d, J=1.7 Hz, 2 H), 0.17-0.21 (m, 9 H). 19F NMR (471 MHz, CDCl3) δ ppm −129.13.

Provenance & Evidence