2-Fluoro-4-nitrobenzamide → 2-Fluoro-4-nitrobenzonitrile

HRID 507485Notes

Reaction equation

HRID 507485 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C[Si](C)(C)O[Si](C)(C)C>ClCCCl>[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]#[N:6]

Participants

4

Reactant 2

HCID 217840942-Fluoro-4-nitrobenzamideHCID 131724018Phosphorus pentoxide hexamethyl disiloxane

Product 1

HCID 27590482-Fluoro-4-nitrobenzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-fluoro-4-nitrobenzamide (0.83 g, 4.6 mmol) and phosphorus pentoxide/hexamethyl disiloxane in 1,2-dichloroethane (20 mL) was heated under nitrogen at 100° C. for 4 hours. Upon cooling, the solution was poured onto a plug of silica gel and washed with hexane (200 mL) followed by 5% methanol/chloroform (400 mL). The methanol/chloroform washes were collected and concentrated under reduced pressure to give 2-fluoro-4-nitrobenzonitrile (0.71 g, 95%) as a beige solid.

Workup

  1. temperatureUpon cooling
  2. additionthe solution was poured onto a plug of silica gel
  3. washwashed with hexane (200 mL)
  4. customThe methanol/chloroform washes were collected
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-49dc3b1513ce4568995f9725c7da2790
Source dataset
uspto-grants-2010_08
Patent number
US07786131B2

Reaction notes

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