Methoxymethyl-triphenylphosphonium chloride → 1-bromo-2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]benzene

Participants

Reaction Steps

In a dried three-necked flask, to a solution of [(methyloxy)methyl](triphenyl) phosphonium chloride (3.59 g, 10.46 mmol) in THF (20 mL) was added BuLi (3.91 mL, 9.77 mmol) dropwise at −78° C. After addition, the reaction mixture was stirred at room temperature for 20 min. Then the reaction mixture was cooled to −78° C. A solution of 3-bromo-2-(methyloxy)benzaldehyde (D99) (1.5 g, 6.98 mmol) in THF (5 mL) to the reaction mixture dropwise. After addition, the reaction mixture was stirred at −78° C. for 2 hour and then warmed to room temperature. The mixture was stirred at room temperature overnight. Then the reaction was quenched with water. The organic phase was separated. The aqueous phase was extracted with EA (10 mL). The combined organic solution was dried over anhydrous sodium sulphate. After filtration, and concentration, the residue was purified by column chromatography (EA/Hexane: 0 to 30%) to give 1-bromo-2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]benzene (D100) (1.43 g). MS (ES): C10H11BrO2 requires 241.9. found 243.0 (M+H+).

Provenance & Evidence