N-bromobutanimide → Methyl 2-(bromomethyl)-6-nitrobenzoate

HRID 511231

Reaktionsgleichung

Reaktionsgleichung von HRID 511231
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1C(=O)N([Br:22])C(=O)C1>ClCCCl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:22][CH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 596057Methyl 2-methyl-6-nitrobenzoate

Produkt 1

HCID 21708527Methyl 2-(bromomethyl)-6-nitrobenzoateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of methyl 2-methyl-6-nitrobenzoate (TL (1996) 37 5425, 15.6 g, 80 mmol), NBS (21.4 g, 120 mmol) and benzoyl peroxide (200 mg, 0.82 mmol) in 1,2-dichloroethane (250 mL) was heated at reflux for 8 h. The reaction mixture was concentrated to dryness and the crude mixture purified by chromatography over silica gel eluting with 2% ethyl acetate/hexanes to afford 10.5 g of methyl 2-(bromomethyl)-6-nitrobenzoate (XXXVI, yield: 65%). 1H NMR (CDCl3, 400 MHz): δ 3.98 (s, 3H), 4.57 (s, 2H), 7.59 (dd, 1H, J=7.8, 8.4 Hz), 7.78 (d, 1H, J=7.8 Hz), 8.1 (d, 1H, J=8.4 Hz).

Aufarbeitung

  1. temperatureat reflux for 8 h
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customthe crude mixture purified by chromatography over silica gel eluting with 2% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-01f9989299b4483988503d0160d577f3
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096624B2

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