Dimethylformamide → Methyl 3-cyano-4-methylbenzoate

温度

100 °C

A mixture of methyl 3-bromo-4-methylbenzoate (compound 1.6, 18 g, 78.58 mmol, 1.00 equiv), Zn(CN)2 (11.1 g, 94.87 mmol, 1.20 equiv), and Pd(PPh3)4 (7.3 g, 6.32 mmol, 0.08 equiv) in N,N-dimethylformamide (250 mL) was stirred under a nitrogen atmosphere at 100° C. overnight. After cooling to room temperature, the reaction was then quenched by careful addition of 200 mL of FeSO4 (aq., sat.) and diluted with ethyl acetate. The resulting mixture was stirred vigorously then filtered through celite and washed with 1 M FeSO4, water, and ethyl acetate. The layers were separated and the aqueous phase was extracted with 2×500 mL of ethyl acetate. The combined organic layers were washed with 3×200 mL of brine, dried over (Na2SO4), and concentrated under reduced pressure. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:50) as eluent to yield 11 g (76%) of the title compound as an off-white solid.

1. temperatureAfter cooling to room temperature
2. customthe reaction was then quenched by careful addition of 200 mL of FeSO4 (aq., sat.)
3. additiondiluted with ethyl acetate
4. stirringThe resulting mixture was stirred vigorously
5. filtrationthen filtered through celite
6. washwashed with 1 M FeSO4, water, and ethyl acetate
7. customThe layers were separated
8. extractionthe aqueous phase was extracted with 2×500 mL of ethyl acetate
9. washThe combined organic layers were washed with 3×200 mL of brine
10. dry with materialdried over (Na2SO4)
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified

ORDレコード

ord-f4e106459252455c839063b69cbd8ec5

出典データセット

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08871790B2