Sodium Bromide → HCID 100834, compound

HRID 1076020Notes

Reaction equation

HRID 1076020 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 hour 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-bd7a0105a3fb404bb8f712111b3351b1
Source dataset
uspto-grants-1976_05
Patent number
US03954818

Reaction notes

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