Water → 6-(2-Bromoethyl)-4-methoxy-1,3-benzodioxole

2.74 g (14 mmol) of 2-(3-methoxy-4,5-methylenedioxyphenyl)ethyl alcohol (3) was dissolved in 10 ml of ethyl ether, to which was added portionwise 1.64 g (6.1 mmol) of phosphorus tribromide in 2 ml of ethyl ether under ice-cooling. The mixture was refluxed under heating for one hour, then cooled and further stirred while adding 10 ml of water and 15 ml of a saturated sodium hydrogencarbonate aqueous solution. The reaction mixture was separated and the ether layer was washed with 10 ml of a saturated saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica column chromatography (eluate: ethyl acetate / n-hexane=1/2) to obtain 1.93 g of 2-(3-methoxy-4,5-methylenedioxyphenyl)ethyl bromide (6) as a crystal with a yield of 53%. Melting point: 78°-79° C.

1. temperaturecooling
2. temperatureThe mixture was refluxed
3. temperatureunder heating for one hour
4. temperaturecooled
5. customThe reaction mixture was separated
6. washthe ether layer was washed with 10 ml of a saturated saline solution
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica column chromatography (eluate: ethyl acetate / n-hexane=1/2)

ORD record

ord-8656f2ccaf6645b8b9f758ff1f78e144

Source dataset

uspto-grants-1988_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04746747