Iodoethane → HCID 67280287, compound

Participants

Reaction Steps

To solution of 4-bromo-3-fluorobenzene-1-sulfonyl chloride (50 g, 0.184 mol) in THF (800 mL) at 0° C. was added hydrazine monohydrate (40-50%, 41.26 g, 0.644 mol) dropwise over 45 minutes. The reaction was stirred for 4 hours at room temperature and then the solvent was removed under reduced pressure to low volume. Heptane (100 mL) was added and the solid was filtered and washed several times with heptanes. The resulting solid was dissolved in ethanol (800 mL). Sodium acetate (90.56 g, 1.104 mol) and ethyl iodide (143.49 g, 0.92 mol) were added and the reaction heated to reflux for 18 hours. The reaction was allow to cool to room temperature, the solvent was removed under reduced pressure to 30% of the initial volume. The reaction mixture was diluted with water (500 mL) and extracted with CH2Cl2 (3×250 mL). The combined organic layers were washed with brine (2×300 mL), dried over Na2SO4, filtered and reduced to dryness to give a yellow oil. The crude was absorbed onto silica and purified (using siica gel column chromatography eluting with cyclohexane/EtOAc 8/2 to give the title compound as yellow solid in 64% yield, 31.70 g.

Provenance & Evidence