4-Bromotoluene → 4'-Methyl-biphenyl-3-carboxylic acid ethyl ester

Magnesium (1.6 g) and p-bromotoluene (10.26 g) in 60 ml of tetrahydrofuran were stirred and warmed until the reaction commenced. When the exothermic reaction had finished, the mixture was refluxed overnight. In a separate flask, 4 ml of DIBAL (1M in toluene) was added to a suspension of bis(triphenylphosphine)palladium(II) chloride (1.4 g) in 100 ml of tetrahydrofuran, followed by ethyl 3-iodobenzoate (11.04 g). To this mixture, the magnesium reagent prepared above was added dropwise, causing an exothermic reaction. The reaction mixture was stirred overnight at room temperature, and then quenched by addition of dilute hydrochloric acid. The mixture was extracted with ether, and the organic layer washed with water, and then saturated brine. The organic layer was separated, dried over sodium sulfate, the solvent evaporated under reduced pressure, and the residue chromatographed on silica gel, eluting with 5% ethyl acetate in heptane, to yield 5.69 g of ethyl 4'-methylbiphenyl-3-carboxylate, a compound of Formula (17), as a pale yellow oil.

1. temperaturewarmed until the reaction commenced
2. customWhen the exothermic reaction
3. temperaturethe mixture was refluxed overnight
4. additionabove was added dropwise
5. customan exothermic reaction
6. customquenched by addition of dilute hydrochloric acid
7. extractionThe mixture was extracted with ether
8. washthe organic layer washed with water
9. customThe organic layer was separated
10. dry with materialdried over sodium sulfate
11. customthe solvent evaporated under reduced pressure
12. customthe residue chromatographed on silica gel
13. washeluting with 5% ethyl acetate in heptane

ORD record

ord-8ade3edc649f4a38a227428b6258ced6

Source dataset

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05428037