5-Bromo-1,2,3-trimethoxybenzene → HCID 178418846, compound
Reaction equation
C([Li:5])CCC.[CH3:6][O:7][C:8]1[CH:9]=[C:10](Br)[CH:11]=[C:12]([O:16][CH3:17])[C:13]=1[O:14][CH3:15]>CCOCC>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([Li:5])[CH:11]=[C:12]([O:16][CH3:17])[C:13]=1[O:14][CH3:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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.