Triethylamine → 2-Fluoro-5-((triisopropylsilyl)ethynyl)phenol

HRID 2240928Notes

Reaction equation

HRID 2240928 reaction equation
[C:1]([Si:3]([CH:10]([CH3:12])[CH3:11])([CH:7]([CH3:9])[CH3:8])[CH:4]([CH3:6])[CH3:5])#[CH:2].Br[C:14]1[CH:15]=[CH:16][C:17]([F:21])=[C:18]([OH:20])[CH:19]=1.C(N(CC)CC)C>CN(C=O)C.C1(P([Pd-](Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu](I)I>[F:21][C:17]1[CH:16]=[CH:15][C:14]([C:2]#[C:1][Si:3]([CH:7]([CH3:9])[CH3:8])([CH:4]([CH3:6])[CH3:5])[CH:10]([CH3:12])[CH3:11])=[CH:19][C:18]=1[OH:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 183421Phenol, 5-bromo-2-fluoro-HCID 2734682(Triisopropylsilyl)acetylene

Product 1

HCID 593053612-Fluoro-5-((triisopropylsilyl)ethynyl)phenol

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178479804HCID 178479804, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of Ethynyl-triisopropyl-silane (1.13 g, 6.20 mmol), 5-bromo-2-fluorophenol (0.955 g, 4.98 mmol), bis(triphenylphosphino)palladium(II) chloride (0.105 g, 0.15 mmol), copper iodide (0.039 g, 0.205 mmol) and triethylamine (2.9 g, 28.7 mmol) in DMF (4.0 mL) is irradiated in the CEM explorer at 80° C. for 30 min. The solvent is removed and the product purified by Flash Chromatography to yield 2-fluoro-5-((triisopropylsilyl)ethynyl)phenol.

Workup

  1. customThe solvent is removed
  2. customthe product purified by Flash Chromatography

Sources & evidence

ORD record
ord-6b105eb3a7664ab69b70e35d3c227fb1
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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