Nitrogen → 2-Bromo-4-chloro-1-methylthiobenzene

Participants

Reaction Conditions

Reaction Steps

A cold (0° C.) solution of 2-bromo-4-chlorobenzenediazonium tetrafluoroborate (5.0 g, 16.3 mmol) in CH3CN (50 mL) was treated portion wise with sodium thiomethoxide (1.15 g, 16.4 mmol) and a strong evolution of gas (N2) was observed. The mixture was warmed up to 23° C., stirred for 0.25 hours and filtered. The filtrate was concentrated in vacuo; the residue was taken up in CH2Cl2, stirred and the solution was then filtered. The CH2Cl2 filtrate was concentrated in vacuo affording a brown syrup that was distilled under vacuum to provide the purified title compound; bp 125° C./0.4 mm, 1.4 g, 37%. 1H NMR (CDCl3) δ7.56 (d, J=2.5 Hz, H-3, 1H), 7.30 (dd, J=2.5 Hz, J=8.6 Hz, H-5, 1H), 7.07 (d, J=8.6 Hz, H-6, 1H), 2.49 (s, CH3, 3H). IR 1569, 1544, 1450, 1434, 1371,1248, 1105, 1024, 868, 803, 784 cm31 1. Anal. Calcd. for C7H6BrClS: C, 35.39; H, 2.55. Found: C, 34.89; H, 2.51.

Provenance & Evidence