Cesium carbonate → 2-(4-Carboxy-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester

HRID 1628168

Reaktionsgleichung

Reaktionsgleichung von HRID 1628168
[Cl:1][C:2]([Cl:26])([Cl:25])[CH2:3][O:4][C:5](=[O:24])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16](CC(O)=O)[CH:15]=1.SC1C=CC([C:32]([OH:34])=[O:33])=CC=1.ClC(Cl)(Cl)COC(=O)C1C=CC=CC=1CBr.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]([Cl:26])([Cl:25])[CH2:3][O:4][C:5](=[O:24])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:32]([OH:34])=[O:33])=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 957384-Mercaptobenzoic acidHCID 668648212-(3-Carboxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl esterHCID 668652492-Bromomethyl-benzoic acid 2,2,2-trichloro-ethyl ester

Produkt 1

HCID 668652432-(4-Carboxy-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The titled compound was prepared according to the method described for 2-(3-carboxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester above from 4-mercapto-benzoic acid (60 mg, 0.389 mmol), 2-bromomethyl-benzoic acid 2,2,2-trichloro-ethyl ester (135 mg, 0.389 mmol), cesium carbonate (152 mg, 0.467 mmol) and DMF (2 mL). The crude material (85 mg, 52%) was used for the next step without further purification; 1H NMR (400 MHz, CDCl3): δ 4.70 (s, 2H), 5.15 (s, 2H), 7.40 (d, 2H), 7.44-7.60 (m, 3H), 7.82 (d, 2H), 7.96 (d, 1H), 12.9 (br s, 1H); Mass spectrum: M−H+ 418.

Aufarbeitung

  1. customThe crude material (85 mg, 52%) was used for the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-13076a8e801046cbb846f35efc4177d6
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785681B2

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