3-Iodotoluene → 1-Mesyl-4-(3-methylphenyl)but-3-yne

HRID 1279372Notes

Reaction equation

HRID 1279372 reaction equation
[S:1]([CH2:5][CH2:6][C:7]#[CH:8])([CH3:4])(=[O:3])=[O:2].I[C:10]1[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=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]=[C:12]([CH3:16])[CH:11]=1)([CH3:4])(=[O:3])=[O:2]

Participants

6

Reactant 2

HCID 122683-IodotolueneHCID 12053774192989-95-0

Product 1

HCID 184279601-Mesyl-4-(3-methylphenyl)but-3-yneYield 49.8%

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), 3-iodotoluene (1.31 g, 6.00 mmol), copper (I) iodide (40 mg), PdCl2(PPh3)2 (70 mg) in 12 mL of Et3N is stirred at room temperature 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 (565 mg, 47%): 1H NMR (CDCl3) 2.31 (s, 3 H), 2.88 (t, J=6.9 Hz, 2 H), 3.07 (s, 3 H), 4.38 (t, J=6.9 Hz, 2 H), 7.20 (m, 4 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-38037c1a9b294d8e8318c0582f421846
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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