Pyridine → 5-(Bromomethyl)-1,2,3-trimethoxybenzene

HRID 357704

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6]O.N1C=CC=CC=1.P(Br)(Br)[Br:22]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][Br:22]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 3,4,5-trimethoxybenzyl alcohol (20.2 g, 0.108 mol) in 300 ml of dry tetrahydrofuran was added 4.12 ml (0.052 mol) of pyridine, and cooled to 0° C. A solution of phosphorous tribromide (4.8 ml, 0.051 mol) in 20 ml of dry tetrahydrofuran was added dropwise to the above solution at 0 ° C. The mixture was stirred for 1 hr. Tetrahydrofuran was concentrated. The residue was then diluted with 200 ml of 10% hydrochloric acid, and then extracted with 200 ml of ethyl acetate. The extract was dried over magnesium sulfate, filtered, concentrated, and dried in vacuum overnight. 3,4,5-Trimethoxybenzyl bromide (27 g, 100% yield) was obtained as a white solid, which can be used without further purification.

Aufarbeitung

concentrationTetrahydrofuran was concentrated
additionThe residue was then diluted with 200 ml of 10% hydrochloric acid
extractionextracted with 200 ml of ethyl acetate
dry with materialThe extract was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customdried in vacuum overnight

Quellen und Nachweise

ORD-Eintrag: ord-d81fec49ae5444638cd057f3f55b7c37
Quelldatensatz: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05840991

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