Diethyl Ether → HCID 22171473, compound

Temperature

0 °C

To a solution of 4-bromo-2-fluorobenzoic acid (2.0 g) in tetrahydrofran (15 ml) was added 2M isobutylmagnesium bromide in diethyl ether (13.5 ml) dropwise on ice-cooling, and the mixture was stirred at 0° C. for 1 hour. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. To the solution of the residue in N,N-dimethylformamide (20 ml) was added methyliodide (1.14 g) and potassium carbonate (1.89 g), and the mixture was stirred at 20° C. for 3 hours. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give methyl 4-bromo-2-isobutylbenzoate (1.5 g) as a colorless oil.

1. temperaturecooling
2. customThe organic layer was separated
3. washwashed with brine
4. dry with materialdried over magnesium sulfate
5. customevaporated
6. additionTo the solution of the residue in N,N-dimethylformamide (20 ml) was added methyliodide (1.14 g) and potassium carbonate (1.89 g)
7. stirringthe mixture was stirred at 20° C. for 3 hours
8. additionThe mixture was diluted with ethyl acetate and water
9. customThe organic layer was separated
10. washwashed with brine
11. dry with materialdried over magnesium sulfate
12. customevaporated
13. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

ORD record

ord-81dff30de20a41f09cd5d4c7288c54c8

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07629366B2