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

HRID 1836050Notes

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-bb40154468144808b2e3ef1cac16de28
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06774248B2

Reaction notes

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