Bromobenzene → 3-Phenylbenzaldehyde

HRID 530494Notes

Reaction equation

HRID 530494 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]([C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1)=[O:9].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.CCOC(C)=O.[Cl-].[Na+].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:2]1([C:14]2[CH:15]=[C:10]([CH:11]=[CH:12][CH:13]=2)[CH:8]=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 7961BromobenzeneHCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acid

Product 1

HCID 1210533-PhenylbenzaldehydeYield 115.8%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 21863594Toluene ethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

In a microwave tube, to a solution of bromo-benzene (0.5 g, 3.18 mmol) dissolved in a 1:1 mixture toluene/EtOH (14 mL), 3-formylphenyl boronic acid (0.573 g, 3.82), palladium-tetrakis(triphenylphosphine) (0.184 g, 0.159 mmol) and 10% Na2CO3 solution (7 mL) were sequentially added. The reaction was run at 100° C. for 30 min under microwave irradiation. The crude product was diluted with AcOEt and brine, and extracted. The organic phase was separated, dried over Na2SO4 and filtered over a pad of celite to give an organic fraction, which was concentrated to dryness to afford the title compound (0.671 g, quant.). 1H NMR (CDCl3): δ 8.23-7.36 (m, 9H), 10.13 (s, 1H).

Workup

  1. additionwere sequentially added
  2. customThe reaction was run at 100° C. for 30 min under microwave irradiation
  3. extractionextracted
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered over a pad of celite
  7. customto give an organic fraction, which
  8. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-014bae20424f4f2bbd395dceb65d7e60
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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