Water → 1-(Bromomethyl)-3-(1,1,2,2-tetrafluoroethoxy)benzene

To a solution of 3-(1,1,2,2-tetrafluoroethoxy)toluene (15 g, 72.1 mmol) in chloroform (200 ml) were added N-bromosuccinimide (14.11 g, 79.3 mmol) and 2,2′-azobis(isobutyronitrile) (590 mg, 3.60 mmol), and the mixture was heated under reflux for 30 min. The reaction solution was cooled and water (100 ml) was added. The mixture was extracted with chloroform. The extract was washed successively with water (100 ml) and saturated brine (100 ml), dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 3-(1,1,2,2-tetrafluoroethoxy)-α-bromotoluene (19.4 g, purity 56%, 53%). This compound was used for the next reaction without further purification.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 30 min
3. temperatureThe reaction solution was cooled
4. extractionThe mixture was extracted with chloroform
5. washThe extract was washed successively with water (100 ml) and saturated brine (100 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

ORD record

ord-a024bc293b034450aa8de5fd5d1e11d1

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2