Bromine → 4-(5-Bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester

HRID 2106036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2106036
[CH2:1]([O:3][C:4](=[O:24])[C:5]([OH:23])([C:19]([F:22])([F:21])[F:20])[CH2:6][C:7]([C:10]1[C:18]2[O:17][CH2:16][CH2:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)([CH3:9])[CH3:8])[CH3:2].[Br:25]Br>C(O)(=O)C.C(=O)(O)[O-].[Na+]>[CH2:1]([O:3][C:4](=[O:24])[C:5]([OH:23])([C:19]([F:21])([F:22])[F:20])[CH2:6][C:7]([C:10]1[C:18]2[O:17][CH2:16][CH2:15][C:14]=2[CH:13]=[C:12]([Br:25])[CH:11]=1)([CH3:9])[CH3:8])[CH3:2]

Komponenten

5

Edukt 2

HCID 24408Bromine2×HCID 469391194-(2,3-Dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester

Produkt 1

HCID 589599534-(5-Bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of 10 g (29 mmol) of 4-(2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester in 20 mL of acetic acid (HOAc) was added dropwise a solution of 1.55 mL (30 mmol) of bromine in 10 nL of HOAc. The reaction was monitored by proton NMR. An additional 0.5 mL of Br2 was added. The mixture was diluted with saturated aqueous sodium bicarbonate and extracted with diethyl ether. The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford 11.7 g (95%) of 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9a3c088142434a30bdd0d3302ef5eb5b
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579469B2

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