Triethylamine → 2-Ethyl-1-fluoro-4-[2-(trimethylsilyl)ethynyl]benzene

HRID 2415257Notes

Reaction equation

HRID 2415257 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH2:9][CH3:10])[CH:3]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].[Li+].[Cl-].C(N(CC)CC)C>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O>[CH2:9]([C:4]1[CH:3]=[C:2]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])[CH:7]=[CH:6][C:5]=1[F:8])[CH3:10]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 433294Lithium ChlorideHCID 226410254-Bromo-2-ethyl-1-fluorobenzene

Product 1

HCID 226410492-Ethyl-1-fluoro-4-[2-(trimethylsilyl)ethynyl]benzene

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-bromo-2-ethyl-1-fluoro-benzene (2.4 g, 11.82 mmol) in N,N-dimethylformamide (100 mL), trimethylsilyl acetylene (2.0 mL, 14.19 mmol), PdCl2(PPh3)2 (500 mg, 0.72 mmol), LiCl (1 g, 23.64 mmol), CuI (25 mg, 0.1 mmol) and triethylamine (3 mL) were added and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was poured into water and extracted with diethyl ether. The extract was dried (Na2SO4) and concentrated. The residue was chromatographed on silica gel (hexanes) to give a brown oil. 1.58 g, 61%.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe extract was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel (hexanes)
  5. customto give a brown oil

Sources & evidence

ORD record
ord-3abf9204343a4dd98c599d4fb9400c59
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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