Methyl iodide → 4-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuran

HRID 1794546Notes

Reaction equation

[Br:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1O.[C:19](=[O:22])([O-])[O-].[K+].[K+].I[CH3:26]>CN(C=O)C>[Br:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:26])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:22][CH3:19]

Participants

Conditions

Temperature: 50 °C

Procedure

4-Bromo-2-(4-hydroxyphenyl)-benzofuran-5-ol 130 (0.601 g, 1.97 mmol) was taken into 25 mL DMF along with potassium carbonate (2.72 g, 19.7 mmol) and iodomethane (2.45 mL, 39.4 mmol). The mixture was heated overnight at 50° C. under a nitrogen atmosphere. The solution was filtered and the filtrate was diluted with ethyl acetate and washed with water (3×), dried over magnesium sulfate filtered and concentrated. The resulting material was purified by column chromatography on silica gel using 10% ethyl acetate in hexane as the eluent to yield the desired product (0.607 g, 92.5%) as a white solid: Mp. 115–117° C.; 1H NMR (DMSO-d6) δ 7.92 (d, 2 H, J=8.8 Hz), 7.60 (d, 1 H, J=8.6 Hz), 7.22 (s, 1 H), 7.09 (d, 1 H, J=8.9 Hz), 7.07 (d, 2 H, J=8.8 Hz), 3.88 (s, 3 H), 3.83 (s, 3 H); MS 333/335 (M+H)+.

Workup

filtrationThe solution was filtered
additionthe filtrate was diluted with ethyl acetate
washwashed with water (3×)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe resulting material was purified by column chromatography on silica gel using 10% ethyl acetate in hexane as the eluent

Sources & evidence

ORD record: ord-98f9436beef84aa0a53bd5b6b9f27926
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022733B2

Reaction notes

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