Phenylacetylene → (Bromoethynyl)benzene

HRID 357712Notes

Reaction equation

HRID 357712 reaction equation
[Br:1][O-].[Na+].[C:4]1([C:10]#[CH:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl-].[NH4+]>C1COCC1>[Br:1][C:11]#[C:10][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 10821PhenylacetyleneHCID 25517Ammonium ChlorideHCID 23673712Sodium hypobromite

Product 1

HCID 136737(Bromoethynyl)benzeneYield 1,001.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium hypobromite [prepared by slow addition of bromine (11 ml) to 10M sodium hydroxide solution (50 ml) and crushed ice (100 g)] was added a solution of phenylacetylene (20.4 g, 19.97 mmol) in THF (10 ml). The two phase mixture was stirred vigorously for 5 hours. Saturated aq. ammonium chloride was added and the mixture was extracted with diethyl ether (3×30 ml). The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure to provide 1-bromo-2-phenyl-acetylene (36.2 g, 99%) as a yellow oil. 1H-NMR; δ (CDCl3), 7.50 (m). IR: Vmax (neat) 2200 cm-1.

Workup

  1. extractionthe mixture was extracted with diethyl ether (3×30 ml)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b36d5227f62345568203eb25a2131f00
Source dataset
uspto-grants-1998_11
Patent number
US05840974

Reaction notes

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