Phenylacetylene → (Bromoethynyl)benzene

HRID 2106864Notes

Reaction equation

HRID 2106864 reaction equation
[OH-].[Na+].[Br:3]Br.[C:5]1([C:11]#[CH:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O.C(COC)OC>[C:5]1([C:11]#[C:12][Br:3])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 10821PhenylacetyleneHCID 14798Sodium HydroxideHCID 24408Bromine

Product 1

HCID 136737(Bromoethynyl)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of sodium hydroxide (31.4 g) in water (160 ml) was cooled to 6° C. and bromine (18 ml) was added dropwise, the temperature being kept below 20° C. Phenylacetylene (20 g) in dimethoxyethane (80 ml) was added over 15 minutes and the mixture was stirred at room temperature for 5 hours. Water (200 ml) was added, and the mixture was extracted with ether (4×60 ml), dried (MgSO4) and the solvents removed at room temperature to yield phenylbromoacetylene.

Workup

  1. custombeing kept below 20° C
  2. extractionthe mixture was extracted with ether (4×60 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvents removed at room temperature

Sources & evidence

ORD record
ord-f7dae8e16e264944a256aa0dcb701645
Source dataset
uspto-grants-1990_06
Patent number
US04931469

Reaction notes

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