Triethylamine → Benzene, 1-(trifluoromethoxy)-3-[2-(trimethylsilyl)ethynyl]-

HRID 606808Notes

Reaction equation

HRID 606808 reaction equation
C(N(CC)CC)C.Br[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=1.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22]>C(OCC)(=O)C.[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:20][Si:21]([CH3:23])([CH3:22])[C:24]#[C:25][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 5199641-Bromo-3-(trifluoromethoxy)benzene

Product 1

HCID 67047416Benzene, 1-(trifluoromethoxy)-3-[2-(trimethylsilyl)ethynyl]-Yield 100%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Add copper (I) iodide (45.0 mg, 0.24 mmol), bis(triphenylphosphine)palladium (II) dichloride (147.4 m g, 0.21 mmol) and triethylamine (2.37 mL, 16.8 mmol), to a solution of 1-bromo-3-trifluoromethoxybenzene (0.62 mL, 4.15 mmol) and trimethylsilylacetylene (0.78 mL, 5.4 mmol), in ethyl acetate (4 mL) and stir at 50° C. for 18h. Cool the reaction mixture to room temperature, concentrate and purify by silica gel chromatography, eluting with hexanes to give the title compound (1.07 g, 100%).

Workup

  1. concentrationconcentrate
  2. custompurify by silica gel chromatography
  3. washeluting with hexanes

Sources & evidence

ORD record
ord-8f9052c887ae4e10a3b47afdb9c32bfd
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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