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

HRID 1259473Notes

Reaction equation

HRID 1259473 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: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]([O:27][CH3:25])[CH:13]=[C:12]([F:20])[C:11]=1[F:21]

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 g, 3 mmol) in dry THF (25 ml) under nitrogen was cooled to −78° C. 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 continued for another 16 hours. TLC indicated incomplete reaction. Ethyl acetate (100 mL) was added to the reaction mixture and the organic layer was washed with water, dried over sodium sulfate and further purified by column chromatography to provide the desired compound as a yellow solid (0.6 g, 47.6%). m/z=424 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-468cad70f1ee4f8781be5ea174e9e48e
Source dataset
uspto-grants-2013_06
Patent number
US08466316B2

Reaction notes

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