Potassium Carbonate → N-(4'-formylbiphenyl-3-ylmethyl)-N-methylbenzamide

HRID 584890Notes

Reaction equation

HRID 584890 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][N:6]([CH3:15])[C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:19]([C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:18]=[CH:17][CH:16]=[C:4]([CH2:5][N:6]([CH3:15])[C:7](=[O:14])[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:3]=2)=[CH:23][CH:22]=1)=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 22341479HCID 22341479, compound

Product 1

HCID 22341491N-(4'-formylbiphenyl-3-ylmethyl)-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

8.8 g (29 mmol) of N-(3-bromo benzyl)-N-methylbenzamide, 8.7 g (58 mmol) of 4-formylbenzene-boronic acid and 125 ml of toluene are introduced into a three-necked flask under argon. 36 ml (72 mmol) of aqueous potassium carbonate solution (2M) are added dropwise, the reaction medium is degassed with argon and 1 g of tetrakis(triphenylphosphine)palladium(0) chloride is added with heating at 90° C. for 24 hours. The reaction medium is poured into water and extracted with dichloromethane, and the organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a column of silica eluded with a mixture of heptane and ethyl acetate (50/50). After evaporation of the solvents, 7.2 g (75%) of the expected product are collected.

Workup

  1. customthe reaction medium is degassed with argon and 1 g of tetrakis(triphenylphosphine)palladium(0) chloride
  2. additionis added
  3. additionThe reaction medium is poured into water
  4. extractionextracted with dichloromethane
  5. customthe organic phase is separated out
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue obtained
  9. customis purified by chromatography on a column of silica
  10. additioneluded with a mixture of heptane and ethyl acetate (50/50)
  11. customAfter evaporation of the solvents, 7.2 g (75%) of the expected product
  12. customare collected

Sources & evidence

ORD record
ord-232438da281841df9732fbfea8c0b0be
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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