Azobisisobutyronitrile → 4-Bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole

HRID 855921Notizen

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH2:20][O:21][CH3:22])=[C:7]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:12]=3[N:13]=2)[CH:8]=1.[Br:23]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:18][C:14]1[C:12]2[N:13]=[C:9]([C:7]3[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[O:19][CH2:20][O:21][CH3:22])[O:10][C:11]=2[CH:17]=[CH:16][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A mixture of 2-(5-methoxy-2-methoxymethoxyphenyl)-4-methylbenzoxazole (F8) (1.78 g, 5.95 mmol), N-bromosuccinimide (1.01 g, 5.95 mmol), and AIBN (82 mg, 0.5 mmol) in CCl4 (100 mL) was refluxed for 15 h under dry N2 gas flowing. The reaction mixture was cooled to 0° C., the precipitation was removed by filtration maintaining the temperature. After the solvent was evaporated, the residue was washed with small amount of ethanol several times to afford a pinkish solid (1.72 g, 76%). 1H-NMR (500 MHz, CDCl3) δ3.57 (s, 3H), 3.88 (s, 3H), 4.96 (s, 2H), 5.27 (s, 2H), 7.05 (dd, 1H, J=8.5, 3.0 Hz), 7.22 (d, 1H, J=8.5 Hz), 7.34 (t, 1H, J=8.0 Hz), 7.42 (d, 1H, J=8.0 Hz), 7.54 (d, 1H, J=8.0 Hz), 7.66 (d, 1H, J=3.0 Hz).

Aufarbeitung

temperaturewas refluxed for 15 h under dry N2 gas
customthe precipitation
customwas removed by filtration
temperaturemaintaining the temperature
customAfter the solvent was evaporated
washthe residue was washed with small amount of ethanol several times

Quellen und Nachweise

ORD-Eintrag: ord-da08ae807ecd4cb68994eda87ea96232
Quelldatensatz: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07262301B1

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