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

HRID 2181553

Reaktionsgleichung

Reaktionsgleichung von HRID 2181553
[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, 1H), 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-1a70e53bb5074c6e80593a27b084e3e2
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06891044B2

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