Sodium Carbonate → HCID 86706838, compound

HRID 2176427Notes

Reaction equation

HRID 2176427 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][C:17]=1[O:18][CH3:19].C([O-])([O-])=O.[Na+].[Na+]>[Pd]>[Cl:11][C:12]1[CH:13]=[C:14]([C:2]2[C:3]([CH:4]=[O:5])=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 3871792-Bromo-5-hydroxybenzaldehydeHCID 32475223-Chloro-4-methoxybenzeneboronic acid

Product 1

HCID 86706838HCID 86706838, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2-bromo-5-hydroxybenzaldehyde (1 mmol), 3-chloro-4-methoxyphenylboronic acid (1 mmol) and Na2CO3 (2 mmol) were dissolved in AcN/H2O (7:3). Then, palladium tetrakistriphenylphosfine (0.03 mmol) was added and the resulting mixture was refluxed until completion. After concentrating the mixture in vacuo the residue was taken up in water and extracted with AcOEt. The combined organic fractions were dried over Na2SO4, filtered, and evaporated. The crude reaction product was purified by means of flash chromatography on silica gel (hexane/AcOEt 5:1) to yield 3′-chloro-4-hydroxy-4′-methoxybiphenyl-2-carbaldehyde as a white solid (93%); m.p.: 168-170° C.

Workup

  1. temperaturethe resulting mixture was refluxed until completion
  2. concentrationAfter concentrating the mixture in vacuo the residue
  3. extractionextracted with AcOEt
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude reaction product
  8. customwas purified by means of flash chromatography on silica gel (hexane/AcOEt 5:1)

Sources & evidence

ORD record
ord-681ddbc519384e8b8351e47bd72f3243
Source dataset
uspto-grants-2015_06
Patent number
US09066938B2

Reaction notes

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