Benzaldehyde → HCID 22000958, compound

HRID 1976345Notes

Reaction equation

HRID 1976345 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:9][C:10]([OH:14])(C#C)[CH3:11].[CH:15](=O)[C:16]1C=CC=CC=1.C(O)(=O)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:9][CH:10]([CH3:11])[OH:14].[NH2:5][C:4]1[CH:3]=[C:2]([C:15]#[CH:16])[CH:8]=[CH:7][CH:6]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 243Benzoic AcidHCID 82582-Methyl-3-butyn-2-olHCID 115623-BromoanilineHCID 11776Triphenylphosphine

Product 1

HCID 22000958HCID 22000958, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 3-bromoaniline (1.72 g, 10 mmol), 2-methyl-3-butyn-2-ol (1.1 g, 13 mmol) and benzaldehyde (0.3 g, 2.8 mmol, containing some benzoic acid) in triethylamine (5 g) was treated with palladium diacetate (11 mg) and triphenylphosphine (197 mg). This mixture was deaerated by bubbling nitrogen and then heated to reflux. CuI (10 mg) was added and the mixture was heated at reflux for 7 hours. Product isolation analogous to Example 2 gave 1.2 g of 3-aminophenylacetylene dimethylcarbinol.

Workup

  1. customby bubbling nitrogen
  2. temperatureheated to reflux
  3. additionCuI (10 mg) was added
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 7 hours

Sources & evidence

ORD record
ord-f8320f02c82441b888027d0ec7a3a8a3
Source dataset
uspto-grants-2001_05
Patent number
US06225499B1

Reaction notes

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