Sodium Carbonate → 1-Phenylnaphthalene-2-carbaldehyde

HRID 1854702Notes

Reaction equation

HRID 1854702 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]=[O:13].C(=O)([O-])[O-].[Na+].[Na+].[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:20]1([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][C:3]=2[CH:12]=[O:13])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 769091-Bromonaphthalene-2-carbaldehyde

Product 1

HCID 534856861-Phenylnaphthalene-2-carbaldehydeYield 84%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

To a suspension of 1-bromo-2-naphthaldehyde (502 mg, 2.14 mmol), sodium carbonate (270 mg, 2.55 mmol), and phenylboronic acid (339 mg, 2.78 mmol) in 4.2 mL of N,N-dimethylformamide/water (2:1) was added palladium acetate (24 mg, 0.11 mmol) under nitrogen. After being stirred at room temperature overnight, the reaction mixture was filtered. The filtrate was diluted with diethyl ether, and the solution was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 85/15) to obtain the title compound as a white powder (416 mg, 84%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. additionThe filtrate was diluted with diethyl ether
  3. washthe solution was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 85/15)

Sources & evidence

ORD record
ord-72aeff9e48014c12968f57f9f6c374c6
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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