Hydrochloric Acid → 5-(2,4,5-Trifluorophenyl)-3-pentyn-1-ol

HRID 2050648Notes

Reaction equation

HRID 2050648 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[F:10].[CH2:11]([OH:16])[CH2:12][CH2:13][C:14]#[CH:15].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C(N(CC)CC)C.[Pd].[Cu]I>[F:10][C:3]1[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=1[CH2:15][C:14]#[C:13][CH2:12][CH2:11][OH:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 675971-Bromo-2,4,5-trifluorobenzeneHCID 793464-Pentyn-1-olHCID 22619264Triphenyl phosphine chloride

Product 1

HCID 200587085-(2,4,5-Trifluorophenyl)-3-pentyn-1-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 1-bromo-2,4,5-trifluorobenzene (5.0 g, 23.7 mmol), 4-pentyn-1-ol (2.4 ml, 26 mmol), palladium bis(triphenylphosphine chloride (5 mg), copper (I) iodide (5 mg) in triethylamine (30 ml) was refluxed under argon for 10 hours. On cooling, the mixture was acidified with dilute hydrochloric acid and was extracted with ethyl ether. Evaporation of the extracts gave an oil, which was purified by chromatography on a silica column using 60% ethyl ether/hexane to give the title alcohol.

Workup

  1. temperaturewas refluxed under argon for 10 hours
  2. temperatureOn cooling
  3. extractionwas extracted with ethyl ether
  4. customEvaporation of the extracts
  5. customgave an oil, which
  6. customwas purified by chromatography on a silica column

Sources & evidence

ORD record
ord-3176bd6e97ba40288a1792136a6e19ff
Source dataset
uspto-grants-1991_05
Patent number
US05013850

Reaction notes

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