5-Bromo-1,2,3-trimethoxybenzene → HCID 178418846, compound

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Reaction Steps

To a stirred solution of n-butyllithium (3.7 mL, 1.6 M in hexane solution, 6.0 mol) in dry ether (40 mL), a solution of 3,4,5-trimethoxyphenylbromide (0.74 g, 3.0 mol) in ether (20 mL) was added under dry nitrogen at −78° C. The solution was stirred for 1 h in order to form 3,4,5-trimethoxyphenyllithum (“TPL”). Substituted tetralone reagent (3.0 mol) was added at −20° C., and the stirring was continued for 2 h (−20° C.—RT). The mixture was partitioned between CH2Cl2 and water, the organic layer was dried over anhydrous sodium sulfate, and, after filtration, the organic layer was concentrated in vacuo to provide a tetrahydronaphthalen-1-ol as a yellow oil. Each compound was purified by column chromatography.

Provenance & Evidence