2-Bromophenol → HCID 21225056, compound

HRID 1584649Notes

Reaction equation

HRID 1584649 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH3:9][N:10]([CH3:14])[CH2:11][C:12]#[CH:13]>C(N(CC)CC)C.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>[CH3:9][N:10]([CH3:14])[CH2:11][C:12]#[C:13][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8]

Participants

5

Reactant 2

HCID 72442-BromophenolHCID 81643N,N-Dimethylpropargylamine

Product 1

HCID 21225056HCID 21225056, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To a deoxygenated solution of o-bromophenol (10.0 g) in triethylamine (120 ml) may be added 1-dimethylamino-2-propyne (2.82 g), bis(triphenylphosphine)palladium(II) chloride (400 mg), and cuprous iodide (54 mg). The mixture may be stirred at room temperature under an atmosphere of argon for approximately 6 hours, heated briefly (ca. 10 minutes) to 60° C. The reaction mixture is then cooled, filtered through diatomaceous earth, and the solvent may be removed by evaporation in vacuo. The residue can then be dissolved in ethyl acetate, washed three times with water, once with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent may be removed by evaporation in vacuo, and the residue may be purified by chromatography over silica gel (50% ethyl acetate in hexanes may be used as the eluant) to give the purified product.

Workup

  1. temperatureheated briefly (ca. 10 minutes) to 60° C
  2. temperatureThe reaction mixture is then cooled
  3. filtrationfiltered through diatomaceous earth
  4. customthe solvent may be removed by evaporation in vacuo
  5. dissolutionThe residue can then be dissolved in ethyl acetate
  6. washwashed three times with water
  7. dry with materialonce with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate
  8. customThe solvent may be removed by evaporation in vacuo
  9. customthe residue may be purified by chromatography over silica gel (50% ethyl acetate in hexanes
  10. customto give the purified product

Sources & evidence

ORD record
ord-5a834d8df62e4a2e8f52903d866b8944
Source dataset
uspto-grants-1999_08
Patent number
US05932745

Reaction notes

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