Benzoyl Peroxide → (6-(Bromomethyl)-2-methoxybenzyl)phthalimide

HRID 8905

Reaktionsgleichung

Reaktionsgleichung von HRID 8905
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:4]=1[CH2:5][C:6]1[CH:16]=[CH:15][CH:14]=[C:8]2[C:9]([NH:11][C:12](=[O:13])[C:7]=12)=[O:10].[Br:22]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(OCC)C>[Br:22][CH2:21][C:17]1[C:4]([CH2:5][C:6]2[CH:16]=[CH:15][CH:14]=[C:8]3[C:9]([NH:11][C:12](=[O:13])[C:7]=23)=[O:10])=[C:3]([O:2][CH3:1])[CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21985073(2-Methoxy-6-methylbenzyl)phthalimide

Produkt 1

HCID 21985106(6-(Bromomethyl)-2-methoxybenzyl)phthalimideAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of (2-methoxy-6-methylbenzyl)phthalimide (0.286 g, 1.02 mmol) in CC4 (25 mL) was added recrystallized N-bromosuccinimide (0.177 g, 0.99 mmol) followed by benzoyl peroxide (28 mg, 0.11 mmol). The resultant mixture was heated to reflux for 90 minutes then cooled to room temperature. The mixture was diluted with diethyl ether (25 mL), filtered through filter paper, and the filtrate was concentrated. Purification of the crude material by column chromatography (3:1 hexanes-EtOAc) provided 0.31 g (86%) of (6-(bromomethyl)-2-methoxybenzyl)phthalimide as a white solid. 1H NMR (CDCl3) δ 3.78 (s, 3H), 4.90 (s, 2H), 5.00 (s, 2H), 6.83 (d, 1H, J=8.4 Hz), 6.98 (d, 1H, J=7.2 Hz), 7.25 (dd, 1H, J=7.2, 8.4 Hz), 7.67–7.69 (m, 2H), 7.78–7.81 (m, 2H). ES-MS m/z 382 (M+Na), 384 (M+Na).

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 (3:1 hexanes-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-5c6876f3a159419d84868a80768d6864
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091217B2

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