Methyl 4-bromobenzoate → HCID 23290991, compound

Temperature

56 °C

A mixture of dry Mg (900 mg, 37 mmol) and ZnBr2 (5.63 g, 25 mmol) in THF (25 mL) was treated with 5-bromopent-1-ene (4.45 mL, 37.6 mmol) and the subsequent suspension was heated at 56° C. for 18 h. The mixture was cooled to room temperature and methyl 4-bromobenzoate (7.1 g, 33 mmol) and tetrakis-triphenylphosphine) palladium(0) (1.0 g, 0.865 mmol) were added, and the mixture was stirred at room temperature for 24 h. The mixture was quenched with 3N HCl (aqueous) and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous MgSO4 and evaporated at reduced pressure. The residue was purified by flash chromatography (silica gel, 5% ethyl acetate/hexane) to give the crude title compound which was used without further purification.

1. temperatureThe mixture was cooled to room temperature
2. customThe mixture was quenched with 3N HCl (aqueous)
3. extractionextracted with ethyl acetate
4. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
5. customevaporated at reduced pressure
6. customThe residue was purified by flash chromatography (silica gel, 5% ethyl acetate/hexane)

ORD record

ord-fc04147fe2864b7c8ffb637bf72c3e9a

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05939412