Methoxymethyl-triphenylphosphonium chloride → (E)-3-bromo-2-methoxy-5-(2-methoxyvinyl)pyridine

Temperature

0 °C

A solution of (methoxymethyl)triphenylphosphonium chloride (737 mg, 2.15 mmol) in THF (10 mL) at −78° C. was added t-BuOK (1 M in THF, 2.15 mL, 2.15 mmol) and stirred at 0° C. for 30 mins, then added dropwisely a solution of 5-bromo-6-methoxynicotinaldehyde (310 mg, 1.435 mmol) in THF (6 mL) at 0° C. via cannulation. The mixture was stirred and gradually warmed to rt overnight. The mixture was concentrated and the residue was purified via a flash column using 50% ethyl acetate in hexanes as an eluent. The product containing fractions were concentrated to give (E)-3-bromo-2-methoxy-5-(2-methoxyvinyl)pyridine (296.9 mg, 85% yield).

1. stirringThe mixture was stirred
2. temperaturegradually warmed to rt overnight
3. concentrationThe mixture was concentrated
4. customthe residue was purified via a flash column
5. additionThe product containing fractions
6. concentrationwere concentrated

ORD record

ord-ff82a8c028e34a3eb395f3bff4fe5835

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410128B2