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

HRID 490398
Notes
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Reaction equation

HRID 490398 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 588241724-(4-Bromo-phenylsulphanylmethyl)-5-methyl-furan-2-carboxylic acid methyl ester

Product 1

HCID 588241845-Methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylsulphanylmethyl]-furan-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 312751,4-DioxaneSolvent

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

  1. temperaturecooled
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washthe organic phase washed with brine
  5. dry with materialdried (MgSO4)
  6. customAfter evaporation of the solvent the residue
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes