Triethylamine → HCID 11290100, compound

HRID 380713Notes

Reaction equation

HRID 380713 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1)#[CH:2].Br[C:11]1[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=1)[C:14]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[O:15].C(N(CC)CC)C>ClCCl>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:24]2[CH:25]=[CH:11][CH:12]=[C:13]([C:14](=[O:15])[C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH:23]=2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5226271-Ethynyl-4-fluorobenzeneHCID 36501933-Bromo-4'-fluorobenzophenone

Product 1

HCID 11290100HCID 11290100, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Into a 500 mL, 3-neck, round-bottom flask equipped with a magnetic stirrer, a thermocouple, and a condenser were placed 24.00 g (200.0 mMol) of 1-ethynyl-4-fluorobenzene (see examples A1 or A2), 55.82 g (200.0 mMol) of 3-bromo-4′-fluorobenzophenone (Rieke Metals, Inc.), 3.0 g of tetrakis(triphenylphosphine)palladium[0], and 300 mL of de-aerated triethylamine. The reaction mixture was heated to 80° C. with stirring under argon for 3 hr and then cooled to ambient; stirring was continued overnight (approximately 16 hr). The reaction mixture was filtered to remove a white precipitate of triethylamine hydrobromide. The triethylamine solvent was evaporated and the solids obtained dissolved in dichloromethane. The resulting solution was washed with water (2×100 mL), 2% HCl (2×100 mL), brine, and then dried over sodium sulfate. After removal of the solvent, the product was purified by silica gel column chromatography using hexanes as the elutant. After removal of the solvent, white crystals with a melting point of 127-128° C. were obtained in a yield of 85%.

Workup

  1. customInto a 500 mL, 3-neck, round-bottom flask equipped with a magnetic stirrer
  2. temperaturecooled
  3. stirringstirring
  4. waitwas continued overnight
  5. custom(approximately 16 hr)
  6. filtrationThe reaction mixture was filtered
  7. customto remove a white precipitate of triethylamine hydrobromide
  8. customThe triethylamine solvent was evaporated
  9. customthe solids obtained
  10. washThe resulting solution was washed with water (2×100 mL), 2% HCl (2×100 mL), brine
  11. dry with materialdried over sodium sulfate
  12. customAfter removal of the solvent
  13. customthe product was purified by silica gel column chromatography
  14. customAfter removal of the solvent, white crystals with a melting point of 127-128° C.
  15. customwere obtained in a yield of 85%

Sources & evidence

ORD record
ord-e9b80c5845ce4b92b72bbe288238ae79
Source dataset
uspto-grants-2001_10
Patent number
US06303733B1

Reaction notes

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