Propargyl bromide → HCID 12786188, compound

HRID 903664Notes

Reaction equation

HRID 903664 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[Mg].[F:6][CH2:7][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12]>CCOCC>[F:6][CH2:7][C:8]([OH:13])([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][C:2]#[CH:1]

Participants

5

Procedure

A 0.25 ml. portion of propargyl bromide is added to a stirred suspension of 0.73 g. of magnesium and 6 mg. of mercuric chloride in 7.5 ml. of ether. The reaction is initiated after a few minutes of vigorous stirring at room temperature. A mixture of 3 g. of 80% 1-fluoro-2-hexanone and 3.63 g. of propargyl bromide in 7.5 ml. of ether is added dropwise through a dropping funnel so that the reaction remains gently refluxing (25° C. to 32° C.). Cooling in a water bath is required. The reaction mixture is cooled in an ice bath, quenched with 8 ml. of cold saturated aqueous ammonium chloride, filtered through Celite and washed with ether. The mother liquor is evaporated to dryness giving a reddish oily residue, which is Kugheror-distilled at 45° C./4 mm giving the product as a colorless liquid.

Workup

  1. waitThe reaction is initiated after a few minutes
  2. additionA mixture of 3 g
  3. temperatureremains gently refluxing (25° C. to 32° C.)
  4. temperatureCooling in a water bath
  5. temperatureThe reaction mixture is cooled in an ice bath
  6. customquenched with 8 ml
  7. filtrationof cold saturated aqueous ammonium chloride, filtered through Celite
  8. washwashed with ether
  9. customThe mother liquor is evaporated to dryness
  10. customgiving a reddish oily residue, which
  11. distillationis Kugheror-distilled at 45° C./4 mm

Sources & evidence

ORD record
ord-f35222422c8b487f82a4796749fef9af
Source dataset
uspto-grants-1980_10
Patent number
US04228298

Reaction notes

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