Tin tetrachloride → 6-Methoxy-7-fluoro-2,2-dimethyl-thiochroman-4-one

Participants

Reaction Steps

To a solution of the acyl chloride (Compound 202, 2.80 g, 10.1 mmol) in 35 mL of CH2Cl2 at 0° C. was added dropwise a solution of SnCl4 (2.64 g, 10.1 mmol) in 5 mL of CH2Cl2. After 2.5 hours the reaction was quenched by the slow addition of 20 mL H2O. The organic layer was washed with 1M aqueous HCl, 5% aqueous NaOH, H2O, and finally saturated aqueous NaCl before being dried over MgSO4. Concentration under reduced pressure afforded 1.90 g (78%) the title compound as a tan solid. 1H NMR (300 MHz, CDCl3)δ: 7.72 (1H, d, J=8.9 Hz), 6.95 (1H, d, J=11.0 Hz), 3.91 (3H, s), 2.85 (2H, s), 1.47 (6H,s).

Provenance & Evidence