N-bromobutanimide → Ethyl 2-bromomethyl-6-methoxybenzoate

HRID 8943

Reaktionsgleichung

Reaktionsgleichung von HRID 8943
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OCC)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:14][C:10]1[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:3]([O:2][CH3:1])[CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 2

HCID 67184N-bromobutanimideHCID 5910602-Methoxy-6-methyl-benzoic acid ethyl ester

Produkt 1

HCID 10038926Ethyl 2-bromomethyl-6-methoxybenzoateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 7187Benzoyl PeroxideKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-methoxy-6-methylbenzoate (0.813 g, 4.19 mmol) in CCl4 (8 mL) was added recrystallized N-bromosuccinimide (0.751 g, 4.22 mmol) followed by benzoyl peroxide (52 mg, 0.22 mmol). The resultant mixture was heated to reflux for 90 minutes then cooled to room temperature. The mixture was diluted with diethyl ether (50 mL), filtered through filter paper, and the filtrate was concentrated. Purification of the crude material by column chromatography (8:1 hexanes-EtOAc) provided 0.68 g (60%) of ethyl 6-(bromomethyl)-2-methoxybenzoate as a colorless oil. 1H NMR (CDCl3) δ 1.42 (t, 3H, J=7.2 Hz), 3.84 (s, 3H), 4.45 (q, 2H, J=7.2 Hz), 4.50 (s, 2H), 6.89 (d, 1H, J=8.4 Hz), 7.01 (d, 1H, J=7.2 Hz), 7.34 (dd, 1H, J=7.2, 8.4 Hz).

Aufarbeitung

  1. temperatureto reflux for 90 minutes
  2. filtrationfiltered
  3. filtrationthrough filter paper
  4. concentrationthe filtrate was concentrated
  5. customPurification of the crude material by column chromatography (8:1 hexanes-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-f64e217233764463aa5656221e71fb06
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091217B2

Verknüpfte Notizen

Wird geladen…