Sodium Carbonate → 4'-Chlorobiphenyl-2-carbaldehyde

HRID 1520583Notes

Reaction equation

HRID 1520583 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 811292-Bromobenzaldehyde

Product 1

HCID 13936894'-Chlorobiphenyl-2-carbaldehyde

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To 2-bromobenzaldehyde (2.3 ml) and tetrakis(triphenylphosphine)palladium(0) (0.35 g) in toluene (50 mL), was added 4-chlorophenylboronic acid (4.0 g) and 2M Na2CO3 (70 ml). The mixture was heated under reflux for one hour. The reaction was cooled, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine and the combined aqueous layers back-extracted with ethyl acetate. The combined organic layers were dried over Na2SO4. The crude material was purified by flash chromatography using 97.5/2.5 hexane/ethyl acetate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for one hour
  3. temperatureThe reaction was cooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. extractionthe combined aqueous layers back-extracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-b86da5a4ebc34df58c1d0806a488025b
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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