tert-Butylanisole → 4-Bromo-2-tert-butyl-1-methoxybenzene

HRID 860559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860559
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Br-:13].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.O>[C:1]([C:5]1[CH:10]=[C:9]([Br:13])[CH:8]=[CH:7][C:6]=1[O:11][CH3:12])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 270626tert-ButylanisoleHCID 21124087Pyridiniumtribromide

Produkt 1

HCID 37338984-Bromo-2-tert-butyl-1-methoxybenzeneAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-(t-butyl)anisole (16.38 g, 0.0997 mol) in CH2Cl2 (350 mL) was added pyridinium tribromide (35.09 g, 0.110 mol). The resulting mixture was allowed to stir at RT overnight. The mixture was diluted with CH2Cl2 and H2O and the layers were separated, the aqueous layer was extracted with CH2Cl2 (2×). The combined organic layers were washed with H2O, brine and dried with MgSO4. The mixture was filtered and the solvents evaporated to give 2-(t-butyl)-4-bromoanisole as an oil (23.16 g, 95%). 1H NMR (300 MHz, CDCl3): δ 1.35 (s, 9H), 3.82 (s, 3H), 6.74 (d, J=8.7 Hz, 1H), 7.28 (dd, J1=8.7 Hz, J2=2.4 Hz, 1H), 7.35 (d, J=2.4 Hz, 1H).

Aufarbeitung

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  3. washThe combined organic layers were washed with H2O, brine
  4. dry with materialdried with MgSO4
  5. filtrationThe mixture was filtered
  6. customthe solvents evaporated

Quellen und Nachweise

ORD-Eintrag
ord-dd7fba94511e47fdb06504b960e675e8
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153875B2

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