Phenethyl bromide → 4-(2-Bromoethyl)benzaldehyde

To a solution of (2-bromoethyl)benzene (100 mmol, 18.5 g) in methylene chloride (185 ml) at 0° C. was added dropwise titanium tetrachloride (200 mmol, 22 ml). The mixture was stirred for 10 minutes and alpha,alpha-dichloromethyl methyl ether (100 mmol, 9 ml) was added dropwise. The reaction mixture was stirred at room temperature for 1 hour and poured into saturated NaHCO3 (1 liter). Ethyl acetate (750 ml) was added and the solution was filtered through diatomaceous earth, the organic layer separated, dried (Na2SO4) and solvent removed in vacuo. The residue was triturated with hexane to afford 8.7 g of title product; m.p. 49°-52° C.

1. stirringThe reaction mixture was stirred at room temperature for 1 hour
2. filtrationthe solution was filtered through diatomaceous earth
3. customthe organic layer separated
4. dry with materialdried (Na2SO4) and solvent
5. customremoved in vacuo
6. customThe residue was triturated with hexane

ORD record

ord-cc3c393625554068af5cd46d89e82ba8

Source dataset

uspto-grants-1991_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05061717