Sodium Carbonate → HCID 71742910, compound

HRID 2207923Notes

Reaction equation

HRID 2207923 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)[CH3:11].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C)C=O>[CH2:10]([O:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=1)[CH3:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 707414-BromobenzaldehydeHCID 27739203-Ethoxybenzeneboronic acid

Product 1

HCID 71742910HCID 71742910, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromobenzaldehyde (4.0 g, 21.6 mmol), 3-ethoxyphenylboronic acid (4.0 g, 21.6 mmol), a 2N sodium carbonate solution (216.0 mL, 216.0 mmol), and Pd(dppf)Cl2 (1.6 g, 2.2 mmol) were added to N,N-dimethylformamide (216.0 mL). The reaction mixture was stirred at 80° C. for 3 hours and then filtered through celite pad. Distilled water was added to the filtrate, which was then extracted with ethyl acetate. The extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5) to give 4.6 g of the titled compound as a pale yellow liquid.

Workup

  1. filtrationfiltered through celite pad
  2. additionDistilled water was added to the filtrate, which
  3. extractionwas then extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow liquid residue
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-8b1f3c4031fb456a876aee945328090a
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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