Water → 4-(2-Fluoro-4-nitrophenyl)butanenitrile

HRID 1192876Notes

Reaction equation

[C:1]([CH2:3][CH2:4][C:5]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[F:23])(C(OC)=O)C(OC)=O)#[N:2].[Cl-].[Na+].O>CS(C)=O>[F:23][C:15]1[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=1[CH2:5][CH2:4][CH2:3][C:1]#[N:2]

Participants

Conditions

Temperature: 21 °C

Procedure

A solution of compound Dimethyl 2-(2-cyanoethyl)-2-(2-fluoro-4-nitrophenyl)malonate (73) (0.19 g, 0.59 mmol), sodium chloride (0.10 g, 1.76 mmol) and water (0.15 mL) in distilled dimethylsulfoxide (DMSO, 4 mL) was heated to 155° C. overnight. The reaction mixture was allowed to cool to 21° C. and then worked up by adding water and extracting with ethyl acetate (2×50 mL). The organic layer was dried over MgSO4, concentrated and the residue was purified with silica gel column chromatography (hexane:ethyl acetate, 8:1) to give desired 4-(2-Fluoro-4-nitrophenyl)butanenitrile (72) (79 mg, 65%): 1H NMR δ 8.02 (dd, 1H, J=8.3, 2.2 Hz), 7.94 (dd, 1H, J=9.5, 2.2 Hz), 7.42 (dd, 1H, J=8.3, 7.4 Hz), 2.93 (t, 2H, J=7.7 Hz) 2.41 (t, 2H, J=7.0 Hz) 2.01-2.07 (m, 2H).

Workup

extractionextracting with ethyl acetate (2×50 mL)
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated
customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate, 8:1)

Sources & evidence

ORD record: ord-075caba61bcb4476956daf5582deeb1a
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680291B2

Reaction notes

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