Hydrochloric Acid → HCID 13572894, compound

HRID 556335Notes

Reaction equation

HRID 556335 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:8].[CH3:9][Si:10]([C:13]#[CH:14])([CH3:12])[CH3:11].Cl>C(N(CC)CC)C.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:14]#[C:13][Si:10]([CH3:12])([CH3:11])[CH3:9]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 127541-Bromo-2-chlorobenzeneHCID 66111Trimethylsilylacetylene

Product 1

HCID 13572894HCID 13572894, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

2-Bromochlorobenzene (54.1 ml, 0.46 mol) and trimethylsilylacetylene (72 ml, 0.51 mol) were dissolved in triethylamine (250 ml). Triphenylphosphine (0.4 g, 1.5 mmol), copper (I) iodide (0.3 g, 1.6 mmol) and bistriphenyphosphinepalladium (II) dichloride (0.5 g, 0.67 mmol) were added and the mixture was heated under reflux for 18 h. The reaction mixture was cooled to ambient temperature and carefully added to 10% hydrochloric acid (480 ml). The product was extracted into hexane (3×200 ml), the extracts were washed with 10% hydrochloric acid (200 ml) and water (2×200 ml) then dried (MgSO4) and evaporated in vacuo to give (2-chlorophenylethynyl)-trimethylsilane (95.4 g) as an orange oil, which was used without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 h
  3. extractionThe product was extracted into hexane (3×200 ml)
  4. washthe extracts were washed with 10% hydrochloric acid (200 ml) and water (2×200 ml)
  5. dry with materialthen dried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1e90292fad9641c0b8dd1b25c6b06b53
Source dataset
uspto-grants-2011_11
Patent number
US08058283B2

Reaction notes

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