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

HRID 2213995Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-11c0c3328a2a4ca58c1e98f56ca133b7
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105680B1

Reaction notes

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