Nitrogen → 4-Bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole

HRID 855908Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:14]=3[N:15]=2)=[C:5]([O:21][CH2:22][O:23][CH3:24])[CH:4]=1.[Br:25]N1C(=O)CCC1=O.N#N>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:25][CH2:20][C:16]1[C:14]2[N:15]=[C:11]([C:6]3[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=3[O:21][CH2:22][O:23][CH3:24])[O:12][C:13]=2[CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 5 (1.39 g, 4.23 mmol), N-bromosuccinimide (0.75 g, 4.23 mmol) and AIBN (33 mg, 0.2 mmol) in CCl4 (70 mL) was refluxed for 15 hours under a flow of dry N2 gas. The reaction mixture was cooled to 0° C. and the precipitate was removed by filtration while maintaining the temperature at 0° C. After the solvent was evaporated, the residue was washed with small amount of ethanol several times to afford a pinkish solid 6 (1.14 g, 66%): 1H-NMR (500 MHz, CDCl3) δ3.60 (s, 3H), 3.97 (s, 3H), 3.99 (s, 3H), 4.96 (s, 2H), 5.31 (s, 2H), 6.85 (s, 1H), 7.30 (t, 1H, J=8.0 Hz), 7.40 (d, 1H, J=8.0 Hz), 7.51 (d, 1H, J=8.0 Hz), 7.66 (s, 1H).

Workup

customthe precipitate was removed by filtration
temperaturewhile maintaining the temperature at 0° C
customAfter the solvent was evaporated
washthe residue was washed with small amount of ethanol several times

Sources & evidence

ORD record: ord-dca0b89717334d3d8a98e0f3661c9306
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262301B1

Reaction notes

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