Sodium Sulfide → 3-Fluoro-2-mercapto-benzoic acid ethyl ester

HRID 1861116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1861116
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=1F)[CH3:2].[S-2:14].[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=1[SH:14])[CH3:2]

Komponenten

7

Edukt 2

HCID 14804Sodium SulfideHCID 2761174Benzoic acid, 2,3-difluoro-, ethyl ester

Produkt 1

HCID 229782253-Fluoro-2-mercapto-benzoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 311Citric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of ethyl-2,3 difluorobenzoate (1.07 g, 5.75 mmol) in DMF (10 mL) was treated with sodium sulfide (896 mg, 11.5 mmol, 2.0 equiv) at 23° C. The mixture was stirred under argon for 10 h. The solution was diluted with ethyl acetate (50 mL) and water (50 mL) and 10% citric acid (5 mL). The organic layer was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, decanted and concentrated under reduced pressure to give 3-Fluoro-2-mercapto-benzoic acid ethyl ester: 1H NMR (300 MHz, CDCl3) δ 7.71 (t, 1H), 7.38 (m, H), 7.12 (m, 1H), 4.41 (q, 2H), 1.40 (t, 3H); LCMS (100% area) Rt=4.53 min, (pos) [M+H]/z Calc'd 201.0, found 200.9.

Aufarbeitung

  1. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. customdecanted
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-04861ba9de7e4ea6af0286bc035ae813
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531491B1

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