Sodium Carbonate → HCID 86639498, compound

HRID 1854720Notes

Reaction equation

HRID 1854720 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[C:17]1(B(O)O)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:10][C:7]1[CH:8]=[CH:9][C:2]([C:25]2[C:26]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:22]=[CH:23][CH:24]=2)=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 3871792-Bromo-5-hydroxybenzaldehyde

Product 1

HCID 86639498HCID 86639498, compoundYield 74.1%

Reagents, catalysts & solvents 2

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

Procedure

To a suspension of 2-bromo-5-hydroxybenzaldehyde (300 mg, 1.49 mmol), sodium carbonate (190 mg, 1.79 mmol), and 1-naphthaleneboronic acid (384 mg, 2.23 mmol) in 3.0 mL of N,N-dimethylformamide/water (2:1) was added palladium acetate (18 mg, 80 μmol) under nitrogen. After being stirred at room temperature overnight, the reaction mixture was filtered. The filtrate was diluted with ethyl acetate, and the solution was washed with saturated NaHCO3 aqueous solution, 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=85/15 to 75/25) to obtain the title compound as a white solid (274 mg, 74%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. additionThe filtrate was diluted with ethyl acetate
  3. washthe solution was washed with saturated NaHCO3 aqueous solution, 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=85/15 to 75/25)

Sources & evidence

ORD record
ord-fe584c55432a4cf6af2d129d9c3ba9de
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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