Hydrochloric Acid → 4-(4-Hydroxy-phenylsulfanyl)-3-nitro-phenol

HRID 883929Notes

Reaction equation

HRID 883929 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C)C=O>[OH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 691274-Chloro-3-nitrophenolHCID 2401474-Mercaptophenol

Product 1

HCID 670403614-(4-Hydroxy-phenylsulfanyl)-3-nitro-phenolYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-Chloro-3-nitro-phenol (2.0 g, 11.52 mmol), 4-hydroxythiophenol (1.45 g, 11.52 mmol) and cesium carbonate (11.26 g, 34.56 mmol) in N,N-dimethylformamide (25 mL) was heated to 100° C. for 4 hours. After cooling to room temperature, 1N aqueous Hydrochloric acid (150 mL) was added and the resultant solution extracted with ethyl acetate (2×100 mL), the combined extracts dried over magnesium sulfate, filtered and concentrated under vacuum to provide the crude title compound which was purified by chromatography on silica gel using hexanes/ethyl acetate as eluent to obtain the title product as a bright orange solid (1.35 g, 45%).

Workup

  1. extractionthe resultant solution extracted with ethyl acetate (2×100 mL)
  2. dry with materialthe combined extracts dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto provide the crude title compound which
  6. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-0cd46077a36d445cb7ebae3444bd54fa
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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