Potassium Carbonate → HCID 19363114, compound

HRID 850317Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1B(O)O.[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18](I)[CH:19]=[C:20]([CH:24]=1)[C:21]([OH:23])=[O:22])=[O:15].C(=O)([O-])[O-].[K+].[K+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][O:13][C:14]([C:16]1[CH:24]=[C:20]([CH:19]=[C:18]([C:3]2[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=2[Cl:1])[CH:17]=1)[C:21]([OH:23])=[O:22])=[O:15]

Participants

Conditions

Temperature: 40 °C

Procedure

The mixture of 2,5-dichlorophenyl-dihydroxyborane (9.35 g), 5-methoxycarbonyl-3-iodobenzoic acid (10 g), potassium carbonate (14.0 g) and palladium(II) acetate (0.073 g) in water (200 ml) was stirred at 40° C. for four hours. Undissolved material was filtered, washed with water (100 ml), suspended in water (150 ml) and adjusted to pH 2.0 with 6N hydrochloric acid. The mixture was extracted two times with a mixture of ethyl acetate (120 ml) and tetrahydrofuran (60 ml), washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residual crystalline was washed with n-hexane to give 3-methoxycarbonyl-5-(2,5-dichlorophenyl)benzoic acid (5.36 g, 50.4%).

Workup

filtrationUndissolved material was filtered
washwashed with water (100 ml)
extractionThe mixture was extracted two times
additionwith a mixture of ethyl acetate (120 ml) and tetrahydrofuran (60 ml)
washwashed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
washThe residual crystalline was washed with n-hexane

Sources & evidence

ORD record: ord-398b578ba74b412c934016ad3ffb988a
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06017917

Reaction notes

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