Benzoyl Peroxide → Methyl 2-bromo-2-(3-fluoro-4-methoxyphenyl)acetate

HRID 1877920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877920
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([F:13])[CH:6]=1.C1C(=O)N([Br:22])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[CH:4]([Br:22])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([F:13])[CH:6]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14897830Methyl 2-(3-fluoro-4-methoxyphenyl)acetate

Produkt 1

HCID 58827055Methyl 2-bromo-2-(3-fluoro-4-methoxyphenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

The (3-fluoro-4-methoxyphenyl)acetic acid methyl ester (5.16 g, 26.0 mmol) is dissolved in carbon tetrachloride (300 mL) along with NBS (5.56 g, 31.3 mmol) and benzoyl peroxide (0.63 g, 2.60 mmol) and refluxed for 2 h. The solution is then allowed to cool to room temperature and is filtered. The filtrate is evaporated and the residue purified via flash column chromatography (EtOAc/hexanes 5:95→EtOAc/hexanes 2:8) to give bromo-(3-fluoro-4-methoxyphenyl)acetic acid methyl ester as a yellow oil. 1H NMR (CDCl3) δ 7.37 (d, J=12 Hz, 1H), 7.26-7.23 (m, 1H), 6.93 (t, J=8 Hz, 1H), 5.31 (s, 1H), 3.91 (s, 3H), 3.81 s, 3H).

Aufarbeitung

  1. temperaturerefluxed for 2 h
  2. filtrationis filtered
  3. customThe filtrate is evaporated
  4. customthe residue purified via flash column chromatography (EtOAc/hexanes 5:95→EtOAc/hexanes 2:8)

Quellen und Nachweise

ORD-Eintrag
ord-c2b2e0c698024afc9c4e62968af8dd65
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314097B2

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