Triethylamine → 3-Cyano-5-nitrobenzotrifluoride

HRID 1050187Notes

Reaction equation

HRID 1050187 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([NH2:9])=O)([O-:3])=[O:2].CCN(CC)CC.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CC(=O)OCC>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)[C:7]#[N:9])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 10537621HCID 10537621, compound

Product 1

HCID 107274333-Cyano-5-nitrobenzotrifluorideYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of 3-nitro-5-(trifluoromethyl)benzamide (1.5 g, 6.41 mmol) in DCM (20 mL) were added Et3N (1.314 mL, 9.61 mmol) and trifluoroacetic anhydride (1.357 mL, 9.61 mmol) at 20° C. The mixture was stirred at 20° C. for 2 h. TLC (PE/EA=3:1, Rf=0.6) showed the reaction was finished. The reaction was concentrated to give crude product, which was purified by column chromatography (PE/EA=3:1, Rf=0.6) to give 3-nitro-5-(trifluoromethyl)benzonitrile (1.2 g, 5.14 mmol, 80% yield): 1H NMR (400 MHz, CDCl3-d) δ 8.71 (s, 2H), 8.24 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated
  2. customto give crude product, which
  3. customwas purified by column chromatography (PE/EA=3:1, Rf=0.6)

Sources & evidence

ORD record
ord-f028d4d1d6934badbd5905e9f4b57524
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

Loading…