Triethylamine → HCID 19821084, compound

HRID 1030871Notes

Reaction equation

HRID 1030871 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].C(N(CC)CC)C.[C:20]1([C:26]#[CH:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:20]1([C:26]#[C:27][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([C:9]([F:12])([F:11])[F:10])[CH:4]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 679604-Bromo-2-(trifluoromethyl)aniline

Product 1

HCID 19821084HCID 19821084, compoundYield 66.7%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A multinecked flask as described in Example 1 was charged with 10.0 g (0.042 mol) of 2-amino-5-bromobenzotrifluoride, 100 ml of dried, degassed triethylamine, 5.32 g (0.052 mol) of phenylacetylene, 0.48 g (0.41 mmol) of tetrakis(triphenylphosphine)palladium(O), 0.1 g (0.38 mmol) of triphenylphosphine, and 0.05 g (0.26 mmol) of cuprous iodide. The reaction mixture was heated at 70° C. for 48 hours at which point thin layer chromatography showed the reaction to be complete. The product mixture was cooled to room temperature and diluted with 50 ml of toluene. Filtration of the triethylamine hydrobromide salt by-product followed by concentration of the filtrate under reduced pressure gave the crude product as a yellow oil. Fractionation under reduced pressure (bp 146°-150° C./1.2 mm Hg) gave 7.22 g (0.028 mol, 66% yield) of the product as a viscous yellow oil.

Workup

  1. customA multinecked flask as described in Example 1
  2. customof dried
  3. customthe reaction
  4. temperatureThe product mixture was cooled to room temperature
  5. filtrationFiltration of the triethylamine hydrobromide salt by-product
  6. customgave the crude product as a yellow oil

Sources & evidence

ORD record
ord-9b415d9a50c143e6ab79eee33c320c14
Source dataset
uspto-grants-1992_04
Patent number
US05107026

Reaction notes

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