Propargyl bromide → HCID 14695612, compound

HRID 619890Notes

Reaction equation

HRID 619890 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[C:13](=[C:16]([CH3:18])[CH3:17])[O:12][C:11]1=[O:19].C(=O)([O-])[O-].[Na+].[Na+].[CH2:26](Br)[C:27]#[CH:28]>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:28][C:27]#[CH:26])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[C:13](=[C:16]([CH3:17])[CH3:18])[O:12][C:11]1=[O:19]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10340Sodium CarbonateHCID 14695585HCID 14695585, compound

Product 1

HCID 14695612HCID 14695612, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile solution (30 ml) of 3-(2'-fluoro-4'-chloro-5'-hydroxyphenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione (0.72 g, 2.5 mmol) was added sodium carbonate (0.16 g), and the mixture was heated at reflux for 1 hour. After the addition of propargyl bromide (0.36 g, 3.0 mmol), the reaction mixture was further refluxed for 1 hour. After the solution was quenched with 0.1N hydrochloric acid, the product was extracted with chloroform. The extracts combined were dried and evaporated as small a volume as possible. The resulting pale yellow oil was purified by silica gel column chromatography to give pure 3-(2'-fluoro-4'-chloro-5'-propargyloxyphenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione. (0.53 g, 65% yield)

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperaturethe reaction mixture was further refluxed for 1 hour
  4. customAfter the solution was quenched with 0.1N hydrochloric acid
  5. extractionthe product was extracted with chloroform
  6. customThe extracts combined were dried
  7. customevaporated as small a volume as possible
  8. customThe resulting pale yellow oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7f134e9e15f24f96afbc1ea7e30de74d
Source dataset
uspto-grants-1989_04
Patent number
US04818272

Reaction notes

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