Benzyl Alcohol → Benzyl 4-bromobutanoate

Temperature

-70 °C

80% Sodium hydride dispersion in oil (0.18 g, 5.9 mmol) was added portionwise to a stirred solution of benzyl alcohol (0.64 g, 5.9 mmol) in anhydrous tetrahydrofuran (10 ml) under nitrogen. After a further 1 hour at room temperature, the reaction mixture was cooled to -70° C. and a solution of 4-bromobutanoyl chloride (1.0 g, 5.4 mmol) in anhydrous tetrahydrofuran (3 ml) added dropwise. After 0.5 hour, the cooling bath was removed and the reaction mixture quenched at room temperature with 5% aqueous ammonium chloride solution (20 ml) and then extracted with dichloromethane (3×20 ml). The combined extracts were washed with saturated brine, dried (Na2SO4) and evaporated under reduced pressure, then the residue was purified by column chromatography on silica gel, eluting with dichloromethane, to give the required ester as a gum. Rf 0.60 (SS 16).

1. waitAfter 0.5 hour
2. customthe cooling bath was removed
3. customthe reaction mixture quenched at room temperature with 5% aqueous ammonium chloride solution (20 ml)
4. extractionextracted with dichloromethane (3×20 ml)
5. washThe combined extracts were washed with saturated brine
6. dry with materialdried (Na2SO4)
7. customevaporated under reduced pressure
8. customthe residue was purified by column chromatography on silica gel
9. washeluting with dichloromethane

ORD record

ord-f33e20107af84fa28fe4514bf77b2341

Source dataset

uspto-grants-1997_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05607960