Triethylamine → HCID 16050020, compound

HRID 496635Notes

Reaction equation

HRID 496635 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N([CH2:20][CH3:21])CC)C>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.Cl[Pd]Cl.CN(C)C=O>[C:2]1([C:20]#[C:21][C:2]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH:11]=[CH:10][CH:9]=[CH:8][CH:3]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 245494Methyl 2-Bromo-5-nitrobenzoate

Product 1

HCID 16050020HCID 16050020, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2-bromo-5-nitrobenzoate (10 g) phenyl acetylene (4.2 ml), triethylamine (100 ml), cuprous iodide(0.4 g),dimethylformamide (200 ml) and bis-(triphenylphosphine)-palladium(II)chloride (1.35 g) was stirred at ambient temperature for 1 hour under an argon atmosphere. The solvents were removed under reduced pressure and the residue treated with 1N, hydrochloric acid (2 L) and then extracted with ethyl acetate (2×300 ml). The combined organic extracts were washed with saturated aequeous sodium bicarbonate solution (100 ml), water (3×100 ml) and brine (100 ml) filtered through phase separating paper and evaporated to dryness. The residue was purified by flash column chromatography on silica using ethyl acetate/hexane(gradient: 0 to 10%) as eluant to give methyl 2-(2-phenylethynyl)-5-nitrobenzoate (compound 76) as a yellow solid (9.98 g).

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionthe residue treated with 1N, hydrochloric acid (2 L)
  3. extractionextracted with ethyl acetate (2×300 ml)
  4. washThe combined organic extracts were washed with saturated aequeous sodium bicarbonate solution (100 ml), water (3×100 ml) and brine (100 ml)
  5. filtrationfiltered through phase
  6. customseparating paper
  7. customevaporated to dryness
  8. customThe residue was purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-c55478bbe71f4f699f15278d6b498ebd
Source dataset
uspto-grants-2005_09
Patent number
US06946468B1

Reaction notes

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