2-Bromoanisole → 2-Allylanisole

Temperatur

0 °C

Under protective gas, 63 mg of magnesium turnings, 126 mg of anhydrous lithium chloride, 4 ml of dry tetrahydrofuran and 2.4 mmol of 2-bromoanisole were reacted at room temperature to give the Grignard compound. Then the dark-colored solution formed was cooled to 0° C. and a solution of 35.3 mg of iron(III) acetylacetonate (5 mol %) in 2 ml of dry tetrahydrofuran was added and the mixture was stirred for five minutes. Then 2 mmol of allyl acetate were added dropwise and the reaction mixture was stirred for 2 h. For workup, hydrolysis was effected with 5 ml of saturated sodium hydrogencarbonate solution and the mixture was extracted three times with 10 ml each time of ethyl acetate. The combined organic phases were dried over magnesium sulfate, concentrated and purified by column chromatography on silica gel (eluent: cyclohexane-ethyl acetate). 95% of theory of 2-allylanisole was isolated.

1. customto give the Grignard compound
2. customThen the dark-colored solution formed
3. stirringthe reaction mixture was stirred for 2 h
4. customFor workup, hydrolysis
5. extractionthe mixture was extracted three times with 10 ml each time of ethyl acetate
6. dry with materialThe combined organic phases were dried over magnesium sulfate
7. concentrationconcentrated
8. custompurified by column chromatography on silica gel (eluent: cyclohexane-ethyl acetate)

ORD-Eintrag

ord-3aa43cced4a443af89af3e5fcf89a650

Quelldatensatz

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09309188B2