Triethylamine → 2-Bromo-1-(3,3-dimethylbut-1-ynyl)-3-methylbenzene

HRID 1029021Notes

Reaction equation

HRID 1029021 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1I.C(N(CC)CC)C.[CH3:17][C:18]([CH3:22])([CH3:21])[C:19]#[CH:20]>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.[Cu]I.C1COCC1>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:20]#[C:19][C:18]([CH3:22])([CH3:21])[CH3:17]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 135123,3-Dimethyl-1-butyneHCID 509981582-Bromo-1-iodo-3-methylbenzene

Product 1

HCID 673457182-Bromo-1-(3,3-dimethylbut-1-ynyl)-3-methylbenzene

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A flask was charged with bis(triphenylphosphine)palladium(II)chloride (0.042 g, 0.060 mmol) and copper(I) iodide (0.023 g, 0.120 mmol) under nitrogen atmosphere. THF (4.6 mL) was added, followed by 2-bromo-1-iodo-3-methylbenzene (0.594 g, 2 mmol), triethylamine (2.3 mL, 16.50 mmol) and 3,3-dimethylbutyne (0.251 mL, 2.040 mmol). The reaction mixture was allowed to stir at RT overnight. The reaction mixture was filtered through a plug of silica gel and the plug was rinsed with Et2O. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (0-2% EtOAc/hexanes). 2-Bromo-1-(3,3-dimethylbut-1-ynyl)-3-methylbenzene was obtained as a light-yellow clear oil.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of silica gel
  2. washthe plug was rinsed with Et2O
  3. customThe solvent was removed under reduced pressure
  4. customthe remaining residue was purified by flash chromatography (0-2% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c519911a5bea480e8167913bbde94c5d
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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