Sodium Carbonate → 99113-85-6

HRID 2407663Notes

Reaction equation

HRID 2407663 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[C:13]([CH:16]=[O:17])[O:14][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.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>[C:1]1([C:11]2[CH:12]=[C:13]([CH:16]=[O:17])[O:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 27570104-Bromo-2-furaldehyde

Product 1

HCID 1354168999113-85-6Yield 78.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Phenylboronic acid (1.46 g) was added to a stirred mixture of 4-bromofuran-2-carbaldehyde (2.00 g) and tetrakis(triphenylphosphine)palladium(0) (0.396 g) in N,N-dimethylformamide (57 mL) and a solution of sodium carbonate (3.03 g) in water (7 mL). The reaction was heated at 110° C. overnight. The resulting mixture was filtered and the filtrate was partitioned between water and diethyl ether. The layers were separated and the aqueous phase was extracted with diethyl ether. The organics were combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (dichloromethane:hexane=9:1) to obtain the title compound (1.55 g) having the following physical data.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customthe filtrate was partitioned between water and diethyl ether
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with diethyl ether
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (dichloromethane:hexane=9:1)

Sources & evidence

ORD record
ord-7eb1e987fb5e4706bae5ccbdbc059625
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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