2-Iodophenol → 1-(3,4-Dimethoxyphenyl)-3-(2-hydroxyphenyl)propan-1-one

HRID 1170942Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:14])[CH:12]=[CH2:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:14])[CH2:12][CH2:13][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(3,4-dimethoxy-phenyl)-prop-2-en-1-ol (236 mg, 1.22 mmol) in THF (2 mL) was added under a nitrogen atmosphere 2-iodophenol (267 mg, 1.22 mmol), cesium carbonate (158 mg, 0.47 mmol) and palladium(II) acetate (8 mg, 0.04 mmol). The reaction mixture was stirred for 4 h at 80° C. After cooling to ambient temperature it was diluted with ethyl acetate (10 mL) and washed with water (10 mL) and brine (10 mL). The aqueous layers were extracted with ethyl acetate (10 mL) and the combined organic layers dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate=90:10 to 60:40) afforded the title compound (155 mg, 45%) as a colourless oil. MS m/e: 285.0 [M−H]

Workup

temperatureAfter cooling to ambient temperature it
washwashed with water (10 mL) and brine (10 mL)
extractionThe aqueous layers were extracted with ethyl acetate (10 mL)
dry with materialthe combined organic layers dried over sodium sulfate
customPurification by chromatography (SiO2, heptane:ethyl acetate=90:10 to 60:40)

Sources & evidence

ORD record: ord-c94b8e8134ec485ca4de33556529700c
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829563B2

Reaction notes

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