Sodium Carbonate → 4'-Chlorobiphenyl-2-carbaldehyde

HRID 1750744Notes

Reaction equation

HRID 1750744 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+]>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.C1(C)C=CC=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

6

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 811292-Bromobenzaldehyde

Product 1

HCID 13936894'-Chlorobiphenyl-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

2-bromobenzaldehyde (25.05 mL, 40.0 g, 216 mmol) was added to toluene (550 mL) and degassed and flushed with nitrogen. 4-chlorophenylboronic acid (43.9 g, 281 mmol), degassed 2M sodium carbonate (757 mL, 1513 mmol), and tetrakis(triphenylphosphine)palladium(0) (5.00 g, 4.32 mmol) were added. The mixture was refluxed for 2.5 hours, cooled, and the phases were separated. The organic layer was extracted with 2M sodium carbonate, and the aqueous layer was back extracted with ethyl ether. The organic portions were combined, dried with brine and then anhydrous sodium sulfate. The solution was concentrated and purified by flash column chromatography on silica gel with 3% ethyl acetate (in hexanes) increasing to 10% ethyl acetate (in hexanes).

Workup

  1. customdegassed
  2. customflushed with nitrogen
  3. additionwere added
  4. temperatureThe mixture was refluxed for 2.5 hours
  5. temperaturecooled
  6. customthe phases were separated
  7. extractionThe organic layer was extracted with 2M sodium carbonate
  8. extractionthe aqueous layer was back extracted with ethyl ether
  9. dry with materialdried with brine
  10. concentrationThe solution was concentrated
  11. custompurified by flash column chromatography on silica gel with 3% ethyl acetate (in hexanes)
  12. temperatureincreasing to 10% ethyl acetate (in hexanes)

Sources & evidence

ORD record
ord-8de35dd1522a4b1bb61988da16812a84
Source dataset
uspto-grants-2015_10
Patent number
US09156856B2

Reaction notes

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