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

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+).

1. additionAfter addition
2. temperatureThen the reaction mixture was cooled to −78° C
3. additionAfter addition
4. stirringthe reaction mixture was stirred at −78° C. for 2 hour
5. temperaturewarmed to room temperature
6. stirringThe mixture was stirred at room temperature overnight
7. customThen the reaction was quenched with water
8. customThe organic phase was separated
9. extractionThe aqueous phase was extracted with EA (10 mL)
10. dry with materialThe combined organic solution was dried over anhydrous sodium sulphate
11. filtrationAfter filtration, and concentration
12. customthe residue was purified by column chromatography (EA/Hexane: 0 to 30%)

ORD record

ord-9ce9bcb8ac0d4477a83bf425ded4758c

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389508B2