Ammonium Chloride → ({4-[(3-Fluorophenyl)methoxy]phenyl}ethynyl)(trimethyl)silane

HRID 2184352Notes

Reaction equation

HRID 2184352 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19].[Cl-].[NH4+]>C1COCC1.C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 224766211-Fluoro-3-[(4-iodophenoxy)methyl]benzene

Product 1

HCID 22476627({4-[(3-Fluorophenyl)methoxy]phenyl}ethynyl)(trimethyl)silane

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A well stirred suspension of 4.0 g (12.2 mmol) of 1-(3-fluorobenzyloxy)-4-iodo-benzene, 0.23 g (1.22 mmol) of cuprous iodide and 0.856 mg (1.22 mmol) of dichloro bis(triphenylphosphine) palladium(II) in a mixture of 20 ml THF and 10 ml triethylamine is treated dropwise with 1.44 g (14.6 mmol) of trimethylsilyl acetylene. The reaction is exothermic. The mixture is stirred overnight at RT, treated with saturated aqueous ammonium chloride and extracted three times with ethyl acetate. The organic phase is dried, concentrated and subjected to flash-chromatography (silica gel, cyclohexane) to yield 3.48 g (95%) of a slightly orange oil. NMR (CDCl3; 300 MHz): 0.24 ppm (s, 9H); 5.06 ppm (s, 2H); 6.85-7.45 ppm (m, 8H).

Workup

  1. stirringThe mixture is stirred overnight at RT
  2. extractionextracted three times with ethyl acetate
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customto yield 3.48 g (95%) of a slightly orange oil

Sources & evidence

ORD record
ord-4e7f55ff111443c98ea684cd3c74b685
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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