Water → 2-[(2-Nitrophenyl)sulfanyl]benzoic acid

HRID 625173Notes

Reaction equation

HRID 625173 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].O.[OH-].[K+]>C(O)(C)C>[N+:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[S:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 54432-Mercaptobenzoic AcidHCID 14797Potassium HydroxideHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 3769782-[(2-Nitrophenyl)sulfanyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 2-mercapto-benzoic acid (30 g, 0.195 mol) in isopropanol (500 mL) at room temperature were added 1-fluoro-2-nitro-benzene (30.2 g, 0.214 mol), water (100 mL) and potassium hydroxide (31.1 g, 0.555 mol). The reaction mixture was stirred at room temperature overnight, quenched with water and diluted with ethyl acetate. The aqueous phase was extracted with ethyl acetate (3×400 mL) and the combined organic extracts were washed with saturated aqueous sodium chloride (500 mL), dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by flash column chromatography on silica gel to give the title compound. ESI-MS (M+1): 276 calc. for C13H9NO4S 275. 1H NMR: (CDCl3, 400 MHz): δ (ppm) 8.12-8.07 (m, 2H), 7.54-7.43 (m, 2H), 7.42-7.39 (m, 2H), 7.35-7.31 (m, 1H), 7.12-7.09 (m, 1H).

Workup

  1. customquenched with water
  2. additiondiluted with ethyl acetate
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×400 mL)
  4. washthe combined organic extracts were washed with saturated aqueous sodium chloride (500 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-03e9cd55f6564189807a25425262894f
Source dataset
uspto-grants-2016_04
Patent number
US09304126B2

Reaction notes

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