Dichloromethane → Naphthalene, 1-chloro-2-methyl-

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Reaction Steps

To the tin compound 20 (1 g, 3.3 mmole) in CH2Cl2 (50 ml) was added N-chlorosuccimimide NCIS (931 mg, 7 mmole). The mixture was stirred overnight. The mixture was washed with saturated solution of NaHCO3, water, brine, dried with anhydrous magnesium sulfate, and concentrated in vacuo to yield 0.7 g of a crude yellowish semi-solid. The crude yellow semi-solid was purified by column chromatography (silica, 100% hexane) to afford 1.2 g of 21 (80%) as a white powder. A simple component was detected by TLC (100%) hexane) Rf, 0.69; NMR (CDCl3) d 2.3 (3H, S, CH3), d 7.2-8.2 (m, 6H, naphthyl).

Provenance & Evidence