Water → 99113-85-6

HRID 1961425Notes

Reaction equation

HRID 1961425 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[O:5][CH:6]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.CCO.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:9]1([C:2]2[CH:3]=[C:4]([CH:7]=[O:8])[O:5][CH:6]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 27570104-Bromo-2-furaldehyde

Product 1

HCID 1354168999113-85-6Yield 97%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

In a screw cap pressure tube, 4-bromofuran-2-carbaldehyde (504 mg, 2.88 mmol) and phenyl boronic acid (491.7, 4.03 mmol) were suspended in a mixture of toluene:EtOH (4:1). Na2CO3 (sat) (6.0 ml) was added. N2 was bubbled through the mixture for 5 minutes. Pd(PPh3)4 (166.4 mg, 0.05 mmol) was added. The tube was sealed and the mixture heated to reflux for 4.0 h. The mixture was allowed to cool. H2O was added and the product extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography (Pet. Ether/EtOAc 90/10→85/15) to afford the title substance in 97% yield.

Workup

  1. customIn a screw cap pressure tube
  2. customN2 was bubbled through the mixture for 5 minutes
  3. customThe tube was sealed
  4. temperaturethe mixture heated
  5. temperatureto reflux for 4.0 h
  6. temperatureto cool
  7. extractionthe product extracted with EtOAc
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified by flash chromatography (Pet. Ether/EtOAc 90/10→85/15)
  12. customto afford the title substance in 97% yield

Sources & evidence

ORD record
ord-015c1fd2210c46c291e2f2215ee2b5a5
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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