Sodium Dithionite → HCID 68483279, compound

HRID 1875056Notes

Reaction equation

HRID 1875056 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[F:9][C:10]1[C:15]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:14]([N+:23]([O-])=O)[CH:13]=[CH:12][C:11]=1[CH3:26]>O.C1COCC1>[F:9][C:10]1[C:15]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:14]([NH2:23])[CH:13]=[CH:12][C:11]=1[CH3:26]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 57973980HCID 57973980, compound

Product 1

HCID 68483279HCID 68483279, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium hydrosulfite (4.42 g, 21.45 mmol) in water (25 mL) was added dropwise to a solution of 2-fluoro-1-methyl-4-nitro-3-(phenyloxy)benzene (0.884 g, 3.58 mmol) in THF (10 mL). The mixture was stirred at room temperature overnight. The reaction mixture was extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue was purified by chromatography (ethyl acetate:hexane) to give [3-fluoro-4-methyl-2-(phenyloxy)phenyl]amine (0.444 g, 51.4%) as a colorless oil, which crystallized after standing overnight. 1H NMR (400 MHz, chloroform-d) δ ppm 7.23-7.33 (m, 2H), 7.03 (t, 1H), 6.94 (d, 2H), 6.83 (t, 1H), 6.51 (dd, 1H), 3.40 (br. s., 2H), 2.18 (d, 3H). ES MS: m/z 217.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (3×25 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-f0be42b86c8c43e48b69efbbae690e56
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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