Ethanol → 3-Fluoro-4-methoxymethoxy-5-vinylbenzoic acid methyl ester

HRID 423245Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH2:12][O:13][CH3:14])=[C:6](Br)[CH:5]=1.[CH2:17](OB(C=C)OCCCC)[CH2:18]CC.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:5]=[C:6]([CH:17]=[CH2:18])[C:7]([O:11][CH2:12][O:13][CH3:14])=[C:8]([F:10])[CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-bromo-5-fluoro-4-methoxymethoxybenzoic acid methyl ester (300 mg) and vinylboronic acid dibutyl ester (226 mg) in toluene (4 mL)-ethanol (2 mL) were added dichlorobis(triphenylphosphine)palladium (II) (36 mg) and an aqueous solution (1 mL) of sodium carbonate (217 mg). The mixture was stirred at 100° C. for 8 hours, and then allowed to stand for cooling down to room temperature. The resulting insoluble materials were filtered through a Celite pad, and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. After concentration in vacuo, the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=30:1, v/v) to give the title compound (190 mg).

Workup

temperaturefor cooling down to room temperature
filtrationThe resulting insoluble materials were filtered through a Celite pad
concentrationthe filtrate was concentrated in vacuo
additionThe residue was diluted with ethyl acetate
washwashed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationAfter concentration in vacuo
customthe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record: ord-35b09a2d5ceb4649ab4ad837e417dca1
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101774B2

Reaction notes

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