Cesium carbonate → 3-(4-Bromo-3-fluoro-phenoxy)-5-methoxymethoxybenzoic acid methyl ester

HRID 2113810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2113810
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:16][O:17][C:18](=[O:30])[C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[C:21]([O:26][CH2:27][O:28][CH3:29])[CH:20]=1>N1C=CC=CC=1.[Cu]=O>[CH3:16][O:17][C:18](=[O:30])[C:19]1[CH:20]=[C:21]([O:26][CH2:27][O:28][CH3:29])[CH:22]=[C:23]([O:25][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([F:9])[CH:4]=2)[CH:24]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 23136427Methyl 3-hydroxy-5-(methoxymethoxy)benzoate

Produkt 1

HCID 687084713-(4-Bromo-3-fluoro-phenoxy)-5-methoxymethoxybenzoic acid methyl esterAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14829Copper oxideKatalysatorHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

After adding 20.4 g (0.68 mol) of 1-bromo-2-fluoro-4-iodobenzene, 20.8 g (0.64 mol) of cesium carbonate and 5.07 g (0.64 mol) of copper (II) oxide to a solution of 9.00 g (0.43 mol) of 5-hydroxy-3-methoxymethoxybenzoic acid methyl ester in pyridine (50.0 ml), the mixture was stirred at 130° C. for 8 hours under a nitrogen atmosphere. The reaction mixture was filtered and then concentrated under reduced pressure, acetic acid ethyl ester and saturated aqueous ammonium chloride were added to the obtained residue, and the organic layer was washed with brine, dried and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=9:1) to obtain 10.6 g of 3-(4-bromo-3-fluoro-phenoxy)-5-methoxymethoxybenzoic acid methyl ester (yield: 65%) as a yellow oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure, acetic acid ethyl ester and saturated aqueous ammonium chloride
  3. additionwere added to the obtained residue
  4. washthe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-54a5897daa0e4307b4dd0897ddd4aecd
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432287B2

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