Hydrochloric Acid → Dimethyl 2-(2-bromophenoxy)benzene-1,4-dicarboxylate

HRID 1803355

Reaktionsgleichung

Reaktionsgleichung von HRID 1803355
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1F.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[Br:16]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 79178Dimethyl 2-fluoroterephthalate

Produkt 1

HCID 57839250Dimethyl 2-(2-bromophenoxy)benzene-1,4-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-fluoro-terephthalic acid dimethyl ester 2j (10 g, 47.1 mmol), 2-bromophenol 1j (6.0 mL, 51.8 mmol) and potassium carbonate (7.16 g, 51.8 mmol) in N,N-dimethylformamide (100 mL) was heated at 100° C. for 36 h. The mixture was allowed to cool to rt, then poured into cold dilute hydrochloric acid (0.5 N, 350 mL). The product was extracted into EtOAc, washed with water (4×) and brine (1×) and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel using dichloromethane as the eluant. The crude product was isolated (10.5 g) and used without further purification in the subsequent reaction. MS: m/z 365 (MH+).

Aufarbeitung

  1. temperatureto cool to rt
  2. extractionThe product was extracted into EtOAc
  3. washwashed with water (4×) and brine (1×)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3b6bbe30d0784a069bed7f4477c767f3
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08350041B2

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