Dimethylformamide → 2-Fluoro-4-(methylsulfonyl)benzonitrile

HRID 2246236Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][C:8]=1[F:17])(=O)=O.[CH3:20][N:21](C=O)C>C(OCC)(=O)C.[Cl-].[Na+].O.[C-]#N.[Zn+2].[C-]#N>[F:17][C:8]1[CH:9]=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=[CH:12][C:7]=1[C:20]#[N:21]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of the product from Step D (662 mg, 2.06 mmol) in DMF (8 mL) was added zinc cyanide (951 mg, 8.1 mmol), and the reaction was then heated at 80° C. for 12 h. The reaction mixture was diluted with ethyl acetate and poured into brine. The organic phase was separated, and the aqueous phase was extracted with two portions of ethyl acetate. The combined organic layers were washed with brine and concentrated in vacuo. Purification by flash chromatography (50:50 hexanes/ethyl acetate) afforded the desired product.

Workup

customThe organic phase was separated
extractionthe aqueous phase was extracted with two portions of ethyl acetate
washThe combined organic layers were washed with brine
concentrationconcentrated in vacuo
customPurification by flash chromatography (50:50 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-49e8a3743ee341ad87cf1910c6d02962
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687492B2

Reaction notes

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