Sodium Carbonate → HCID 11287711, compound

HRID 1854716Notes

Reaction equation

HRID 1854716 reaction equation
Br[C:2]1([CH:9]=[CH:8][CH:7]=[CH:6][CH2:5]1)[CH:3]=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[C:16]1(B(O)O)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:24]1([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[CH:3]=[O:4])[C:25]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 86639494HCID 86639494, compound

Product 1

HCID 11287711HCID 11287711, compoundYield 87.1%

Reagents, catalysts & solvents 2

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

Procedure

To a suspension of 1-bromobenzaldehyde (200 μL, 1.71 mmol), sodium carbonate (218 mg, 2.06 mmol), and 1-naphthaleneboronic acid (353 mg, 2.05 mmol) in 3.4 mL of N,N-dimethylformamide/water (2:1) was added palladium acetate (20 mg, 89 μmol) 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=90/10 to 80/20) to obtain the title compound as a white solid (346 mg, 87%).

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=90/10 to 80/20)

Sources & evidence

ORD record
ord-0086a11b3f014c0f86fdf90618d81426
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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