Sodium Methoxide → HCID 86669363, compound

HRID 574100Notes

Reaction equation

HRID 574100 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:19])[CH:13]=[C:12](F)[C:11]=1[F:21].[CH3:22][O-:23].[Na+]>C1COCC1.C(OCC)(=O)C>[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:19])[CH:13]=[C:12]([O:23][CH3:22])[C:11]=1[F:21]

Participants

5

Reactant 2

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

Product 1

HCID 86669363HCID 86669363, compoundYield 456.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-fluoro-N-(2,3,5-trifluoro-6-nitrophenyl)-4-iodobenzeneamine (2.55 g, 6.16 mmol) in THF (40 mL), was slowly added NaOMe solution (25% in MeOH, 1.4 mL, 0.62 mmol) at −78° C. The mixture becomes dark in color immediately. After the addition was complete, the reaction mixture was warmed to rt and stirred overnight. It was then diluted with ethyl acetate and washed with water, brine and then dried. After removal of volatiles, the crude product was purified by silica gel flash column using 2-10% ethyl acetate/hexanes as eluent to produce the desired product as yellow powder (1.2 g, 48%). Unreacted starting material 2-fluoro-N-(2,3,5-trifluoro-6-nitrophenyl)-4-iodobenzeneamine (1 g) was also recovered.

Workup

  1. customat −78° C
  2. additionAfter the addition
  3. washwashed with water, brine
  4. customdried
  5. customAfter removal of volatiles
  6. customthe crude product was purified by silica gel flash column

Sources & evidence

ORD record
ord-7c1b33f475ff435d998bb9122eb4ee89
Source dataset
uspto-grants-2015_05
Patent number
US09034861B2

Reaction notes

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