Methoxymethyl-triphenylphosphonium chloride → HCID 58168572, compound

Temperature

-78 °C

To a solution of [(methyloxy)methyl](triphenyl)phosphonium chloride (2.1 g, 6.13 mmol) in Tetrahydrofuran (THF) (40 mL) stirred under nitrogen at 0° C. was added BuLi (4.08 mL, 6.53 mmol) dropwise. The reaction mixture was stirred at −78° C. for 30 min. Then a solution of 3-bromo-2-methylbenzaldehyde (D93) (1 g, 5.02 mmol) in Tetrahydrofuran (THF) (40 mL) was added dropwise. The reaction mixture was continuously stirred overnight. The reaction was quenched with sat. aq. NH4Cl. The aqueous layers were separated and extracted with EA for 3 times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate. The dried solution was concentrated, and purified by ISCO column chromatography (PE: EA=8:2) to afford (E)-2-(3-bromo-2-methylphenyl)ethenyl methyl ether (D94) (938 mg) as a yellow oil. MS (ES): C10H11BrO requires 255.9. found 227 (M+H+)

1. waitThe reaction mixture was continuously stirred overnight
2. customThe reaction was quenched with sat. aq. NH4Cl
3. customThe aqueous layers were separated
4. extractionextracted with EA for 3 times
5. washThe combined organic layers were washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationThe dried solution was concentrated
8. custompurified by ISCO column chromatography (PE: EA=8:2)

ORD record

ord-941ea6bd60a044d1997a02b553243fe6

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389508B2