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

HRID 923240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923240
[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-337ea27808bf47a2af7b7956e565da1e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278969B2

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