Water → 2-Fluoro-4-[2-(4-propylphenyl)ethynyl]bromobenzene

HRID 850236Notes

Reaction equation

HRID 850236 reaction equation
[F:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][C:7]=1[Br:8].[CH2:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][CH:14]=1)[CH2:11][CH3:12].O>C(NCC)C.[Cu](I)I>[F:1][C:2]1[CH:3]=[C:4]([C:20]#[C:19][C:16]2[CH:17]=[CH:18][C:13]([CH2:10][CH2:11][CH3:12])=[CH:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[Br:8]

Participants

6

Reactant 3

HCID 962WaterHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 27751331-Ethynyl-4-propylbenzene

Product 1

HCID 193623862-Fluoro-4-[2-(4-propylphenyl)ethynyl]bromobenzeneYield 100%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8021DiethylamineSolvent

Procedure

To a solution of 33 mmol of 3-fluoro-4-bromo iodobenzene, 0.6 mmol of copper iodide and 1.1 mmol of dichlorobistriphenylphosphine palladium in 100 ml of diethylamine were added dropwise 33 mmol of 4-propyl phenylacetylene under an argon stream while stirring. After completion of the addition, the solution was stirred at room temperature for a further 2 hours and placed into water. The solution was extracted with heptane, washed with water and concentrated under reduced pressure to afford a brown oily product. The product was isolated and purified by a silica gel column chromatography to afford 33 mmol of 2-fluoro-4-[2-(4-propylphenyl)ethynyl]bromobenzene as a pale yellow oily product.

Workup

  1. additionAfter completion of the addition
  2. stirringthe solution was stirred at room temperature for a further 2 hours
  3. extractionThe solution was extracted with heptane
  4. washwashed with water
  5. concentrationconcentrated under reduced pressure
  6. customto afford a brown oily product
  7. customThe product was isolated
  8. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-912c48c59f4c4e99907b410c0245686a
Source dataset
uspto-grants-2000_01
Patent number
US06017467

Reaction notes

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