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

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Reaction Steps

To a stirred solution of n-butyllithium (0.5 mL, 1.6 M in hexane solution, 0.80 mol) in dry ether (20 mL), a solution of 3,4,5-trimethoxyphenylbromide (98.8 mg, 0.40 mol) in ether (10 mL) was added under dry nitrogen at −78° C. The solution was stirred for 1 h in order to form 3,4,5-trimethoxyphenyllithum. 7-[(tertButyldimethylsilyl)oxy]-6-methoxy-1-tetralone (122 mg, 0.40 mol) was added at −20° C., and stirring was continued for 2 h (−20° C.—rt). The mixture was partitioned between CH2Cl2 and water, and the organic layer was dried over anhydrous sodium sulfate. After filtration, the organic layer was concentrated in vacuo to provide (35) as a yellow oil.

Provenance & Evidence