Sodium Dithionite → HCID 68487875, compound

HRID 1874935Notes

Reaction equation

HRID 1874935 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[Br:9][C:10]1[CH:11]=[C:12]([O:17][C:18]2[C:23]([F:24])=[C:22]([CH3:25])[CH:21]=[CH:20][C:19]=2[N+:26]([O-])=O)[CH:13]=[C:14]([Cl:16])[CH:15]=1>O.C1COCC1>[Br:9][C:10]1[CH:11]=[C:12]([O:17][C:18]2[C:23]([F:24])=[C:22]([CH3:25])[CH:21]=[CH:20][C:19]=2[NH2:26])[CH:13]=[C:14]([Cl:16])[CH:15]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 684855692-[(3-Bromo-5-chlorophenyl)oxy]-3-fluoro-4-methyl-1-nitrobenzene

Product 1

HCID 68487875HCID 68487875, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Sodium hydrosulfite (37.7 g, 216 mmol) dissolved in water (200 mL) was added dropwise to a vigorously stirred solution of 2-[(3-bromo-5-chlorophenyl)oxy]-3-fluoro-4-methyl-1-nitrobenzene (13.0 g, 36.1 mmol) dissolved in THF (100 mL). The reaction was stirred for 16 h at 40° C. The layers were separated and the aqueous phase was extracted with EtOAc (2×100 mL). The organic extracts were combined, dried over Na2SO4, filtered and concentrated. The crude oil was purified by column chromatography (5% to 100% EtOAc/hexanes gradient) to afford the title compound (5.0 g, 42%) as a light tan solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.39-7.38 (m, 1H), 6.98-6.97 (m, 1H), 6.90-6.85 (m, 2H), 6.54-6.52 (m, 1H), 2.08 (s, 3H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude oil was purified by column chromatography (5% to 100% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-45f8f5592c0d4643adffb1544c04c6fc
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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