N-bromobutanimide → 1-(Bromomethyl)-4-chloro-2-iodobenzene

HRID 1348883

Reaktionsgleichung

Reaktionsgleichung von HRID 1348883
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([I:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:10][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[I:9]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 141766Benzene, 4-chloro-2-iodo-1-methyl-

Produkt 1

HCID 129309611-(Bromomethyl)-4-chloro-2-iodobenzeneAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-2-iodo-1-methylbenzene (3.95 g, 15.6 mmol), N-bromosuccinimide (3.10 g, 17.6 mmol), and benzoyl peroxide (0.1 g) in carbon tetrachloride (100 mL) was heated to reflux for 48 hours, filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4:100 ethyl acetate/hexanes to provide 3.34 g (64%) of the desired product. MS (DCI/NH3) m/z 330, 332 (M+H)30; 1H NMR (CDCl3) δ 7.85 (d, 1H), 7.40-7.32 (m, 2H), 4.59 (s, 2H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 48 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 4:100 ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0c73544aaf074639b176ee31bd481435
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211595B2

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