Reaktion #645642

Reaktionsgleichung

3-bromo-2-chloro-4-picoline

NaH

water

(4-methoxyphenyl)methanol

→

2-(4-methoxybenzyloxy)-3-bromo-4-methylpyridine

Lösungsmittel

EtOAc

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 1 hr
2. 2
   WaschenAfter washing with water and brine
3. 3
   Trocknenthe organic fraction was dried with sodium sulfate
4. 4
   Sonstigepurified by silica gel chromatography

Vorschrift

To a mixture of 60% NaH in mineral oil (0.290 g, 7.27 mmol) in THF (15 mL) at RT in a resealable pressure vessel was added (4-methoxyphenyl)methanol (0.906 ml, 7.27 mmol). After 5 minutes, 3-bromo-2-chloro-4-picoline (1.00 g, 4.84 mmol) was added and the mixture was heated to 75° C. After 1 hr, water was added and the mixture was diluted with EtOAc. After washing with water and brine, the organic fraction was dried with sodium sulfate and purified by silica gel chromatography using 0-30% EtOAc:hexanes to afford 2-(4-methoxybenzyloxy)-3-bromo-4-methylpyridine as a colorless oil. M+H+=308.0.

Quelle