Ethyl Acetate → 2,3-Difluoro-N-(2-fluoro-4-iodophenyl)-5-methoxy-6-nitroaniline

HRID 1176846Notes

Reaction equation

HRID 1176846 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14](F)[CH:13]=[C:12]([F:20])[C:11]=1[F:21].C[O-].[Na+].[C:25](OCC)(=[O:27])C>C1COCC1>[F:21][C:11]1[C:12]([F:20])=[CH:13][C:14]([O:27][CH3:25])=[C:15]([N+:16]([O-:18])=[O:17])[C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 574300722,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline

Product 1

HCID 593863122,3-Difluoro-N-(2-fluoro-4-iodophenyl)-5-methoxy-6-nitroanilineYield 47.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of (2-fluoro-4-iodo-phenyl)-(2,3,5-trifluoro-6-nitro-phenyl)-amine (1.23 gm, 3 mmol) in dry THF (25 ml) was cooled to −78° C. under nitrogen, and a solution of 25% sodium methoxide (0.68 ml, 0.3 mmol) was added slowly. The reaction mixture was allowed to warm to room temperature, and stirring was continued for another 16 hours. TLC indicated incomplete reaction. Ethyl acetate (100 ml) was added to the reaction mixture, and the mixture was washed with water. The organic layer was dried over sodium sulfate and further purified by column chromatography to provide a yellow solid (0.6 gm, yield: 47.6%).

Workup

  1. customreaction
  2. washthe mixture was washed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customfurther purified by column chromatography

Sources & evidence

ORD record
ord-8ec88329956047a9b56adfb89be4b9f7
Source dataset
uspto-grants-2010_11
Patent number
US07842836B2

Reaction notes

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