Sodium Carbonate → 2′-Bromo[1,1′-biphenyl]-4-carboxaldehyde

HRID 1422336Notes

Reaction equation

HRID 1422336 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1.[Br:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1I>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 114151-Bromo-2-iodobenzeneHCID 312751,4-DioxaneHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 13927612′-Bromo[1,1′-biphenyl]-4-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

To a solution of 4-formylbenzeneboronic acid (1.19 g, 7.96 mmol) and Na2CO3 (1.68 g, 15.8 mmol) in water (60 mL) was added p-dioxane (60 mL). This mixture was treated sequentially with 2-bromo iodobenzene (2.25 g, 7.95 mmol) and palladium (II) acetate (159 mg, 0.708 mmol) and allowed to stir at ambient temperature for 16 hours. The solvent was evaporated in vacuo. To the residue was added EtOAc (400 mL) and water (300 mL). The aqueous layer was extracted with EtOAc (2×200 mL). The organic extracts were combined, washed with brine (200 mL), 5% aq. Na2S2O3 (200 mL), brinel (200 mL), dried, (Na2SO4) and the solvent evaporated in vacuo to afford the title compound which was used in the next step without further purification.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionTo the residue was added EtOAc (400 mL) and water (300 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
  4. washwashed with brine (200 mL), 5% aq. Na2S2O3 (200 mL)
  5. customdried
  6. custom(Na2SO4) and the solvent evaporated in vacuo

Sources & evidence

ORD record
ord-a871e56da12f417d95b31d6ac9cdeb1e
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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