Sodium Carbonate → HCID 11287711, compound

HRID 1040385Notes

Reaction equation

HRID 1040385 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].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:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[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 811292-BromobenzaldehydeHCID 2545321-Naphthaleneboronic acid

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 2-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 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=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 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=90/10 to 80/20)

Sources & evidence

ORD record
ord-b69bca30ded74207873c0bdbd2d8a78b
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

Loading…