Hydrochloric Acid → 1-(4-n-Propylphenyl)-2-trimethylsilylacetylene

HRID 493030

Reaction equation

HRID 493030 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(N(CC)CC)C.Cl>[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 1363741-Bromo-4-propylbenzene

Product 1

HCID 193534011-(4-n-Propylphenyl)-2-trimethylsilylacetyleneYield 87.1%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

To 15.0 g (75.4 mmol) of 1-n-propyl-4-bromobenzene were added 8.8 g (89.8 mmol) of trimethylsilylacetylene and 100 ml of triethylamine (NEt3), and the reaction system was purged with argon. Next were added 81 mg (0.4 mmol) of copper (I) iodide (CuI), 324 mg (1.2 mmol) of triphenylphosphine, and 162 mg of dichlorobistriphenylphosphine palladium (II) [PdCl2(PPh3)2] to the reaction system, and the mixture was subjected to reaction for 24 hours with heating and refluxing. After completion of the reaction, the reaction mixture was poured into an iced water, and the resultant mixture was acidified by adding hydrochloric acid. After the resultant water-insoluble oil was extracted with hexane, the hexane phase was washed with water. By removing hexane from the hexane phase, 14.2 g (65.7 mmol) of 1-(4-n-propylphenyl)-2-trimethylsilylacetylene was obtained.

Workup

  1. customthe reaction system was purged with argon
  2. customthe mixture was subjected to reaction for 24 hours
  3. temperaturewith heating
  4. temperaturerefluxing
  5. customAfter completion of the reaction
  6. extractionAfter the resultant water-insoluble oil was extracted with hexane
  7. washthe hexane phase was washed with water
  8. customBy removing hexane from the hexane phase

Sources & evidence

ORD record
ord-41c7fd2116914f8b8f5c9d25ee7d1452
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Linked notes

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