Dimethylformamide → Methyl 5-cyano-2,4-dimethylbenzoate

A solution of methyl 5-iodo-2,4-dimethylbenzoate (compound 2.2, 9.2 g, 31.71 mmol, 1.00 equiv), Zn(CN)2 (4.46 g, 38.12 mmol, 1.20 equiv), and Pd(PPh3)4 (2.93 g, 2.54 mmol, 0.08 equiv) in N,N-dimethylformamide (120 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 100 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 2×100 mL of ethyl acetate. The combined organic layers were washed with 2×20 mL of brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:5) as eluent to yield 6.2 g (93%) of the title compound as a white solid.

1. customthe reaction was then quenched by careful addition of 100 mL of FeSO4 (aq., sat.)
2. additiondiluted with ethyl acetate
3. filtrationthen filtered through celite
4. washwashed with 1 M FeSO4, water, and ethyl acetate
5. customThe layers were separated
6. extractionthe aqueous phase was extracted with 2×100 mL of ethyl acetate
7. washThe combined organic layers were washed with 2×20 mL of brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified

ORD record

ord-c0e1d7a606124648ad51b950920f5de2

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2