Pyridine → Benzene, ((2-bromoethoxy)methyl)-

To an ice-cooled mechanically stirred solution of 2-benzyloxyethanol (25 mL, 0.18 mole), triphenylphosphine (115.2 g, 0.44 mole) and pyridine (56.9 mL, 0.70 mole) in methylene chloride (1000 mL) was added, dropwise, carbon tetrabromide (61.3 g, 0.18 mole). The mixture was stirred overnight at room temperature. Methanol (130 mL) was then added and, after further stirring for 1 hour, the solvents were evaporated. The residue was triturated with hexane and the hexane solution was concentrated to yield an oil which was set aside. The residue remaining after trituration was taken up in ethyl acetate, washed with saturated sodium bicarbonate solution and brine and was concentrated to afford a brown oil. This was triturated with hexane. The resulting hexane solution was combined with the oil from the previous trituration and concentrated. The residue was chromatographed twice on silica gel eluting with hexane and then 5% ethyl acetate/hexane to afford (2-bromoethoxymethyl)benzene as an oil (28.8 g, 76% yield).

1. additionwas added
2. stirringafter further stirring for 1 hour
3. customthe solvents were evaporated
4. customThe residue was triturated with hexane
5. concentrationthe hexane solution was concentrated
6. customto yield an oil which
7. washwashed with saturated sodium bicarbonate solution and brine
8. concentrationwas concentrated
9. customto afford a brown oil
10. customThis was triturated with hexane
11. concentrationconcentrated
12. customThe residue was chromatographed twice on silica gel eluting with hexane

ORD record

ord-5f402683188042b3a200e7b9b54005af

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05854275