Water → 4-(2-Bromoethyl)benzaldehyde

To a solution of dichloromethyl methyl ether (62 ml) in methylene chloride (40 ml) was added titanium tetrachloride (75 ml) over 10 minutes under a nitrogen atmosphere at 4-5° C. Then, a solution of phenethyl bromide (85 ml) in methylene chloride (50 ml) was added thereto over 50 minutes at 5-7° C. and the mixture was stirred for 5 hours while gradually raising the temperature of the mixture to room temperature. Water (200 ml) was added to the reaction mixture over 1 hour and the mixture was extracted with chloroform (200 ml). The chloroform layer was washed with water, a saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure to give a brown oily substance (167 g). The obtained brown oily substance was purified by silica gel column chromatography (eluent; hexane: ethyl acetate=20:1) to give 4-(2-bromoethyl)benzaldehyde (32.3 g) as a yellow solid, melting point 50-52° C.

1. extractionthe mixture was extracted with chloroform (200 ml)
2. washThe chloroform layer was washed with water
3. dry with materiala saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate
4. distillationthe solvent was distilled away under reduced pressure
5. customto give a brown oily substance (167 g)
6. customThe obtained brown oily substance was purified by silica gel column chromatography (eluent; hexane: ethyl acetate=20:1)

ORD record

ord-a6e20d09f11d400dbf970895d2eefd4c

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06214873B1