Sodium Methoxide → HCID 86669364, compound

HRID 574087Notes

Reaction equation

HRID 574087 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([F:18])[CH:12]=[C:11](F)[C:10]=2[F:20])=[C:4]([F:21])[CH:3]=1.[CH3:22][O-:23].[Na+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([F:18])[CH:12]=[C:11]([O:23][CH3:22])[C:10]=2[F:20])=[C:4]([F:21])[CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86669362HCID 86669362, compound2×

Product 1

HCID 86669364HCID 86669364, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-bromo-2-fluoro-phenyl)-(2,3,5-trifluoro-6-nitro-phenyl)-amine (Intermediate 13, 1.5 g, 4.1 mmol) in THF (10 mL) was dropwise added NaOMe solution [prepared by dissolving Na metal (100 mg, 4.1 mmol) in methanol (10 mL)] at −78° C. After complete addition, the reaction mixture was warmed to room temperature and stirred for 1 h. The progress of reaction was monitored by TLC. After completion, the reaction mixture was concentrated under reduced pressure and residue obtained was purified by flash column chromatography to yield (4-bromo-2-fluoro-phenyl)-(2,5-difluoro-3-methoxy-6-nitro-phenyl)-amine as a yellow solid (912 mg).

Workup

  1. customat −78° C
  2. additionAfter complete addition
  3. customThe progress of reaction
  4. concentrationAfter completion, the reaction mixture was concentrated under reduced pressure and residue
  5. customobtained
  6. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-4470029f98444b248d105694d51c730d
Source dataset
uspto-grants-2015_05
Patent number
US09034861B2

Reaction notes

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