Dimethylformamide → HCID 57804234, compound

HRID 2102932Notes

Reaction equation

HRID 2102932 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([Cl:12])[CH:3]=1.[CH:13]1([C:16]#[CH:17])[CH2:15][CH2:14]1.CN(C=O)C>C1(C)C=CC=CC=1.CCN(CC)CC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:12][C:4]1[CH:3]=[C:2]([C:17]#[C:16][CH:13]2[CH2:15][CH2:14]2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

8

Reactant 3

HCID 6228DimethylformamideHCID 138823CyclopropylacetyleneHCID 22058730Methyl 4-Bromo-2-chlorobenzoate

Product 1

HCID 57804234HCID 57804234, compoundYield 76%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of methyl 4-bromo-2-chlorobenzoate (450 mg, 0.0018 mol), copper(I) iodide (34 mg, 0.00018 mol), 70% solution of cyclopropylacetylene (0.26 g, 0.0027 mol) in toluene and bis(triphenylphosphine)palladium(II) chloride (130 mg, 0.00018 mol) in Et3N (5 mL) and DMF (3 mL) was heated at 100° C. in a 50 mL sealed reaction vessel for 36 hours. After cooling, the mixture was filtered through Celite® and the filter cake was washed repeatedly with ethyl acetate. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the product (320 mg, 76%) as a brown oil.

Workup

  1. customsealed
  2. customreaction vessel for 36 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite®
  5. washthe filter cake was washed repeatedly with ethyl acetate
  6. washThe organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f4f32a3c6fdf4147b820b6f773289a68
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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