Water → 5-(3-Bromophenyl)-2-furaldehyde

HRID 446062

Reaction equation

HRID 446062 reaction equation
[CH:1]([C:3]1[O:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].[Br:11][C:12]1[CH:13]=[C:14](I)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:11][C:12]1[CH:17]=[C:16]([C:6]2[O:7][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 27343555-Formylfuran-2-boronic acid

Product 1

HCID 8405175-(3-Bromophenyl)-2-furaldehydeYield 25.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

5-Formyl-2-furanboronic acid (676 mg, 4.8 mmol) and 3-bromoiodobenzene (1132 mg, 4 mmol) were dissolved in 1,2-dimethoxyethane (30 mL), tetrakis(triphenylphosphine)palladium (228 mg, 0.2 mmol) was added thereto, 2 mol/L sodium carbonate (9.6 mL) was further added thereto, and the mixture was heated to reflux for 2 hours while stirring. After the reaction was completed water (20 mL) was added thereto, and extraction with ethyl acetate (20 mL×2) was carried out. The organic layer was washed with saturated brine, water was removed using anhydrous sodium sulfate, the solvent was then removed by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (3/7 (volume ratio)) as an eluent, to give 5-(3-bromophenyl)furan-2-carbaldehyde in a yield of 306 mg (yield 25.9%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. additionwas added
  4. extractionextraction with ethyl acetate (20 mL×2)
  5. washThe organic layer was washed with saturated brine, water
  6. customwas removed
  7. customthe solvent was then removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-5e7c749d4a9446d4a9a263f8c69dd32d
Source dataset
uspto-grants-2013_07
Patent number
US08476449B2

Linked notes

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