Iodobenzene → 1-Mesyl-4-phenylbut-3-yne

HRID 1279368Notes

Reaction equation

HRID 1279368 reaction equation
[S:1]([CH2:5][CH2:6][C:7]#[CH:8])([CH3:4])(=[O:3])=[O:2].I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCN(CC)CC.[Cu]I.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>[S:1]([CH2:5][CH2:6][C:7]#[C:8][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])(=[O:3])=[O:2]

Participants

6

Reactant 2

HCID 11575IodobenzeneHCID 12053774192989-95-0

Product 1

HCID 184279661-Mesyl-4-phenylbut-3-yneYield 52.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 1-mesylbut-3-yne (758 mg, 5.10 mmol), iodobenzene (1.25 g, 6.00 mmol), copper(I) iodide (40 mg), PdCl2(PPh3)2 (70 mg) in 12 mL of Et3N is stirred under N2 for 20 hr. The mixture is filtered and washed with Et3N (3×15 mL). The filtrate is evaporated in vacuo and is purified by flash chromatography to give the product as a pale yellow oil (560 mg, 50%) 1H NMR (CDCl3) 2.91 (t, J=6.6 Hz, 2 H), 4.39 (t, J=6.6 Hz, 2 H), 7.30 (m, 3 H), 7.38 (m, 2 H).

Workup

  1. filtrationThe mixture is filtered
  2. washwashed with Et3N (3×15 mL)
  3. customThe filtrate is evaporated in vacuo
  4. customis purified by flash chromatography

Sources & evidence

ORD record
ord-32221973148e4f6692304b69ed769a41
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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