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

HRID 891176Notes

Reaction equation

HRID 891176 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

HCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 178418846HCID 178418846, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Sources & evidence

ORD record
ord-8f1c728ed30e4d51b79a48435105349a
Source dataset
uspto-grants-2006_02
Patent number
US07001926B2

Reaction notes

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