Water → 1-Bromo-2-methoxy-6-(4-methoxyphenyl)naphthalene

HRID 895177

Reaktionsgleichung

Reaktionsgleichung von HRID 895177
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[CH:4]=1.[Br:21]Br.O>C(O)(=O)C>[Br:21][C:4]1[C:5]2[C:10](=[CH:9][C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[O:2][CH3:1]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24408BromineHCID 111497342-Methoxy-6-(4-methoxyphenyl)naphthalene

Produkt 1

HCID 111636961-Bromo-2-methoxy-6-(4-methoxyphenyl)naphthaleneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

To a mixture of 2-methoxy-6-(4-methoxyphenyl)naphthalene (9.68 g, 36.6 mmol) and glacial acetic acid (150 mL) was slowly added a solution of bromine (5.85 g, 36.6 mmol) in glacial acetic acid (20 mL). The mixture was stirred for 1 hour and the resulting suspension was poured into water (200 mL) and the solid product was collected by filtration. The solid was triturated first with water and then with ethyl acetate to yield 11.25 g (90%) of the title compound as a white solid: mp 172-174° C.; 1H NMR (CDCl3): δ 3.88 (3H, s), 4.05 (3H, s), 7.04 (2H, d, J=8.56 Hz), 7.30 (1H, d, J=9.01 Hz), 7.67 (2H, d, J=8.65 Hz), 7.81 (1H, dd, J=1.61 Hz, J=8.84 Hz), 7.87 (1H, d, J=9.04 Hz), 7.94 (1H, d, J=1.47 Hz), 8.27 (1H, d, J=8.92 Hz); MS (EI) m/z 343 (M)+.

Aufarbeitung

  1. filtrationthe solid product was collected by filtration
  2. customThe solid was triturated first with water

Quellen und Nachweise

ORD-Eintrag
ord-32399ce89bf94e0192952c589451be8c
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06914074B2

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