Triethylamine → ((2-Fluoro-5-nitrophenyl)ethynyl)trimethylsilane

HRID 586295Notes

Reaction equation

HRID 586295 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.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>[F:8][C:7]1[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=1[C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 696992-Bromo-1-fluoro-4-nitrobenzene

Product 1

HCID 12687357((2-Fluoro-5-nitrophenyl)ethynyl)trimethylsilane

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-4-fluoronitrobenzene (2 g, 9.1 mmol) in tetrahydrofuran (30 ml) was added triethylamine (1.9 ml, 13.6 mmol), trimethylsilylacetylene (1.9 ml, 13.6 mmol), triphenylphosphine (60 mg, 0.23 mmol) and dichlorobis(triphenylphosphine)palladium(II) (319 mg, 0.46 mmol). After stirring at room temperature for 20 minutes copper(I) iodide (17 mg, 0.09 mmol) was added and the mixture left to stir for 18 h at room temperature. The reaction mixture was quenched into isohexane (150 ml) and filtered through a plug of silica using isohexane as eluent. The solvent was removed in vacuo to leave (2-fluoro-5-nitrophenylethynyl)trimethylsilane as a brown solid: 1H NMR (360 MHz, CDCl3) δ 0.10 (9H, s), 7.02 (1H, dd, J 8, 1 Hz), 7.97-8.02 (1H, m), 8.17 (1H, dd, J 6, 3 Hz).

Workup

  1. additionwas added
  2. waitthe mixture left
  3. customThe reaction mixture was quenched into isohexane (150 ml)
  4. filtrationfiltered through a plug of silica
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-917a75a523c34420b0536670b1b42d8b
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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