Sodium Carbonate → 3-(pyridin-4-yl)benzaldehyde

HRID 2205293Notes

Reaction equation

HRID 2205293 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH:39]=[O:40]>CC(O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:1]1[CH:6]=[CH:5][C:4]([C:36]2[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=2)[CH:39]=[O:40])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 765833-BromobenzaldehydeHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 27955633-(pyridin-4-yl)benzaldehydeYield 67.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 21889133Propan-2-ol--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

Into a 2 L 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of pyridin-4-ylboronic acid (30 g, 244 mmol, 1 equiv) in 2-propanol/water (800/40 mL), Na2CO3 (77.3 g, 729 mmol, 3 equiv), Pd(OAc)2 (5.46 g, 24.3 mmol, 0.1 equiv), PPh3 (12.75 g, 48.7 mmol, 0.2 equiv) and 3-bromobenzaldehyde (45 g, 243 mmol, 1 equiv). The mixture was stirred for 48 h at 80° C. in an oil bath. Then the solids were filtered out and the filtrate was concentrated under vacuum. The residue was purified by column chromatography on silica gel (eluting with 1:1 ethyl acetate/petroleum ether) to give 30 g of 3-(pyridin-4-yl)benzaldehyde as orange oil.

Workup

  1. customInto a 2 L 3-necked round-bottom flask, purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. filtrationThen the solids were filtered out
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe residue was purified by column chromatography on silica gel (eluting with 1:1 ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-7f66f8008bf34783b0ce3da21ab6e398
Source dataset
uspto-grants-2016_06
Patent number
US09371285B2

Reaction notes

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