Sodium Bromide → HCID 100834, compound

HRID 597697Notes

Reaction equation

HRID 597697 reaction equation
S(O[CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][C:17]#[C:18][CH2:19][CH3:20])(C1C=CC(C)=CC=1)(=O)=O.[Br-:21].[Na+]>CN(C)C=O>[Br:21][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][C:17]#[C:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 253881Sodium BromideHCID 53748711HCID 53748711, compound

Product 1

HCID 100834HCID 100834, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 42.7 g. of 1-tosyloxynon-4-en-6-yne (0.14 moles) in 150 ml. of anhydrous dimethylformamide is added 18.7 g. of sodium bromide (0.16 moles) and the mixture is heated at 75° for 2 hours and then allowed to stir overnight at room temperature. The reaction mixture is then diluted with 200 ml. of ice water and extracted with pentane. The pentane extract is washed with water and dried over sodium sulfate. Evaporation of solvent in vacuo and distillation of the residual oil gave 24.3 g. of 1-bromonon-4-en-6-yne (84% yield) b.p. 52°-55° at 0.15 mm.

Workup

  1. additionThe reaction mixture is then diluted with 200 ml
  2. extractionof ice water and extracted with pentane
  3. extractionThe pentane extract
  4. washis washed with water
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of solvent
  7. distillationin vacuo and distillation of the residual oil
  8. customgave 24.3 g

Sources & evidence

ORD record
ord-3a8273af7f4a4c7290cb19f7e6ec4868
Source dataset
uspto-grants-1977_03
Patent number
US04014946

Reaction notes

Loading…