Triethylamine → ((3,4-Difluorophenyl)ethynyl)trimethylsilane

HRID 606794Notes

Reaction equation

HRID 606794 reaction equation
C(N(CC)CC)C.Br[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[CH:10]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>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>[F:16][C:11]1[CH:10]=[C:9]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH:14]=[CH:13][C:12]=1[F:15]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 676754-Bromo-1,2-difluorobenzene

Product 1

HCID 67047877((3,4-Difluorophenyl)ethynyl)trimethylsilaneYield 100.6%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
50 °C

Procedure

Add copper (I) iodide (109.4 mg, 0.57 mmol), bis(triphenylphosphine)palladium (II) dichloride (365 mg, 0.52 mmol) and triethylamine (5.88 mL, 41.6 mmol), to a solution of 4-bromo-1,2-difluorobenzene (1.17 mL, 10.4 mmol) and trimethylsilylacetylene (1.89 mL, 13.5 mmol), in ethyl acetate (8 mL). Stir at 50° C. for 18h. Cool to room temperature, concentrate and purify the residue by silica gel chromatography, eluting with hexanes, to give the title compound (2.20 g, 100%).

Workup

  1. temperatureCool to room temperature
  2. concentrationconcentrate
  3. custompurify the residue by silica gel chromatography
  4. washeluting with hexanes

Sources & evidence

ORD record
ord-a32602843c3e41318d4223dc3aee1ed5
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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