Dichloromethane → 5-Methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylsulphanylmethyl]-furan-2-carboxylic acid methyl ester

HRID 490398Notes

Reaction equation

ClCCl.[CH3:4][C:5]1([CH3:12])[C:9]([CH3:11])([CH3:10])[O:8][BH:7][O:6]1.[CH3:13][O:14][C:15]([C:17]1[O:18][C:19]([CH3:31])=[C:20]([CH2:22][S:23][C:24]2[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=2)[CH:21]=1)=[O:16]>O1CCCC1.O1CCOCC1>[CH3:13][O:14][C:15]([C:17]1[O:18][C:19]([CH3:31])=[C:20]([CH2:22][S:23][C:24]2[CH:29]=[CH:28][C:27]([B:7]3[O:8][C:9]([CH3:11])([CH3:10])[C:5]([CH3:12])([CH3:4])[O:6]3)=[CH:26][CH:25]=2)[CH:21]=1)=[O:16]

Participants

Conditions

Temperature: 100 °C

Procedure

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (30 mg) and 4,4,5,5-tetramethyl-[1,3,2]dioxaborolan (2.34 ml of a 1M solution in tetrahydrofuran) were added to a degassed solution of 4-(4-bromo-phenylsulphanylmethyl)-5-methyl-furan-2-carboxylic acid methyl ester (150) (400 mg, 1.17 mmoles) in 1,4-dioxan (120 ml). The mixture was heated at 100° C., under an argon atmosphere, for 20 hours, cooled and evaporated. The residue was partitioned between ethyl acetate and water, and the organic phase washed with brine and dried (MgSO4). After evaporation of the solvent the residue was purified by flash chromatography, using heptane/ethyl acetate 9:1 v/v as eluent, to afford compound 151 (212 mg) as a colourless oil.

Workup

temperaturecooled
customevaporated
customThe residue was partitioned between ethyl acetate and water
washthe organic phase washed with brine
dry with materialdried (MgSO4)
customAfter evaporation of the solvent the residue
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-a797fdbecb6b4330bdf6e9b9e19158df
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528157B2

Reaction notes

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