2-Mercaptoethanol → 4-(2-Hydroxyethylthio)-3-nitrobenzoic acid

HRID 2421836Notes

Reaction equation

HRID 2421836 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[SH:14][CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:17][CH2:16][CH2:15][S:14][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 144391134-(2-Hydroxyethylthio)-3-nitrobenzoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-3-nitrobenzoic acid (15 g, 81 mmol) in DMF (250 ml) was added 2-mercaptoethanol (6.27 ml, 89 mmol), and potassium carbonate (28.0 g, 203 mmol). The reaction was allowed to stir over night. The reaction mixture had turned solid and yellow. TLC analysis indicated consumption of starting material. The reaction mixture was treated with H2O (300 mL) and extracted with DCM (2×100 mL). The aqueous layer was then treated with concentrated HCl until a pH of 1 was attained. The organic layer was extracted with EtOAc (4×150 mL). The combined EtOAc extracts were dried over Na2SO4 and concentrated in vacuo to provide 4-(2-hydroxyethylthio)-3-nitrobenzoic acid (19.24 g, 79. mmol) in 98% yield, which was used without further purification.

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture was treated with H2O (300 mL)
  3. extractionextracted with DCM (2×100 mL)
  4. additionThe aqueous layer was then treated with concentrated HCl until a pH of 1
  5. extractionThe organic layer was extracted with EtOAc (4×150 mL)
  6. dry with materialThe combined EtOAc extracts were dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdb49565eb284b61929bc3a5e235655f
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

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