Benzaldehyde → HCID 22000958, compound

HRID 1976341Notes

Reaction equation

HRID 1976341 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9](=O)[C:10]1C=CC=CC=1.C(O)(=O)C1C=CC=CC=1.[CH3:26][C:27]([OH:31])(C#C)[CH3:28]>Cl[Pd]Cl.[Cu]I.C(N(CC)CC)C>[CH3:26][CH:27]([CH3:28])[OH:31].[NH2:6][C:5]1[CH:4]=[C:3]([C:9]#[CH:10])[CH:2]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 243Benzoic AcidHCID 78074-BromoanilineHCID 82582-Methyl-3-butyn-2-ol

Product 1

HCID 22000958HCID 22000958, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-bromoaniline (1.72 g, 10 mmol), benzaldehyde (0.27 g free of benzoic acid, 2.5 mmol), benzoic acid (20 mg, 0.16 mmol), PdCl2 (2 mg) and triethylamine (3.5 g) was deaerated by bubbling nitrogen and then heated to reflux for 30 min. The reaction mixture was cooled to 50° C. and treated with triphenylphosphine (73 mg in 0.5 g of TEA) followed by 2-methyl-3-butyn-2-ol (1.1 g, 13 mmol) and then CuI (20 mg in 1 g TEA). This mixture was heated at reflux for 12 hr. Thin layer chromatography showed the reaction to form 3-aminophenylacetylene dimethylcarbinol, in mixture with N-benzylidene 3-aminophenylacetylene dimethylcarbinol, to be complete.

Workup

  1. customby bubbling nitrogen
  2. temperatureheated
  3. temperatureto reflux for 30 min
  4. additiontreated with triphenylphosphine (73 mg in 0.5 g of TEA)
  5. temperatureThis mixture was heated
  6. temperatureat reflux for 12 hr
  7. customthe reaction

Sources & evidence

ORD record
ord-26deebafc5b04a20a4d34d99c554001e
Source dataset
uspto-grants-2001_05
Patent number
US06225499B1

Reaction notes

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