4-Toluenesulfonyl chloride → Bromopropargyl p-Toluenesulfonate

HRID 35811Notes

Reaction equation

HRID 35811 reaction equation
[Br:1][CH:2]([OH:5])[C:3]#[CH:4].[OH-].[Na+].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>O.O1CCCC1>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O:5][CH:2]([Br:1])[C:3]#[CH:4])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 57294564HCID 57294564, compound

Product 1

HCID 18321753Bromopropargyl p-ToluenesulfonateYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a 100 mL 3-necked round bottom flask, equipped with a magnetic stirrer, nitrogen inlet, thermometer, addition funnel, and ice bath, were placed bromopropargyl alcohol (5 g, 0.037 mole) and tetrahydrofuran (10 mL). A cold solution of NaOH (2.2 g, 0.55 mole) in water (10 mL) was added. To the above stirred mixture a solution of p-toluenesufonyl chloride (7.06 g, 0.037 mole) in tetrahydrofuran (10 mL) was slowly added. The reaction mixture was stirred at 0°-5° C. for 4 hrs. The reaction mixture was then poured into ice water and the resultant white precipitate was collected by suction-filtration and washed with water. After drying in air, an off-white solid was obtained yielding 9.9 g (92.5% yield) m.p. =43°-46° C. An NMR (CDCl3) spectrum indicated the desired compound (V, R3 =p-tolyl). This compound is used in the next example without further purification.

Workup

  1. customIn a 100 mL 3-necked round bottom flask, equipped with a magnetic stirrer, nitrogen inlet
  2. additionthermometer, addition funnel, and ice bath
  3. filtrationthe resultant white precipitate was collected by suction-filtration
  4. washwashed with water
  5. customAfter drying in air
  6. customan off-white solid was obtained
  7. customyielding 9.9 g (92.5% yield)
  8. custom=43°-46° C

Sources & evidence

ORD record
ord-fa33ae58b84f4623a75e65e4066dd828
Source dataset
uspto-grants-1995_05
Patent number
US05411933

Reaction notes

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