Sodium Chloride → 4-(2-Fluoro-4-nitrophenyl)butanenitrile

HRID 1504959Notes

Reaction equation

HRID 1504959 reaction equation
[C:1]([CH2:3][CH2:4][CH:5]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[F:19])C(OC)=O)#[N:2].[Na+].[Cl-]>CS(C)=O.O>[F:19][C:11]1[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=1[CH2:5][CH2:4][CH2:3][C:1]#[N:2]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 68292723Methyl 4-cyano-2-(2-fluoro-4-nitrophenyl)butanoate

Product 1

HCID 576726254-(2-Fluoro-4-nitrophenyl)butanenitrileYield 170.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
160 °C

Procedure

A mixture of compound 66 (1.2 g, 4.5 mmol), NaCl (0.8 g, 13.5 mmol) and water (1.4 mL) in DMSO (30 mL) was stirred at 160° C. for 24 h under N2. After cooling, the mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified with silica gel column chromatography (PE:EtOAc=5:1) to give the compound 67 (1.6 g, 43%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ7.99-8.04 (m, 1H), 7.91-7.96 (m, 1H), 7.38-7.44 (m, 1H), 2.93 (t, 2H, J=7.5 Hz), 2.41 (t, 2H, J=7.0 Hz), 1.98-2.07 (m, 2H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified with silica gel column chromatography (PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-7a3ce36ea6b747f7a728def0e7405ad0
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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