Triethylamine → [2-(3-Methanesulfonylphenyl)ethynyl]trimethylsilane

HRID 1910194Notes

Reaction equation

HRID 1910194 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:3]=1.C(N(CC)CC)C.[C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])#[CH:20]>C1C=CC=CC=1.[Cu]I>[CH3:11][S:8]([C:4]1[CH:3]=[C:2]([C:20]#[C:19][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:7]=[CH:6][CH:5]=1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 2757146Benzene, 1-bromo-3-(methylsulfonyl)-

Product 1

HCID 59240077[2-(3-Methanesulfonylphenyl)ethynyl]trimethylsilaneYield 95%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 241BenzeneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 0.23 g (1 mmol) of 1-bromo-3-methanesulfonyl-benzene in benzene (2 mL) was added 40 mg (0.1 mmol) of PdCl2(Ph3P)2, 30 mg (0.1 mmol) CuI, triethylamine (1 mL) and 0.3 mL of ethynyl-trimethyl-silane. The reaction mixture was heated at 70° C. for 3 h After removal of solvent, the residue was purified by column chromatography elution with hexanes/ethyl acetate (v/v=7:1 then 5:1) to give 0.24 g (95%) of (3-methanesulfonyl-phenylethynyl)-trimethylsilane. 1H NMR (CDCl3, 400 MHz): δ 8.4 (s, 1H), 7.88 (d, 1H), 7.70 (d, 1H), 7.52 (dd, 1H), 3.05 (s, 3H), 0.27 (s, 9H) ppm.

Workup

  1. customAfter removal of solvent
  2. customthe residue was purified by column chromatography elution with hexanes/ethyl acetate (v/v=7:1

Sources & evidence

ORD record
ord-f835cc45e0604fe3abea2fe812746f85
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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