Methyl 4-bromobenzoate → Methyl 4-[(4-butylphenyl)ethynyl]benzoate

HRID 551924Notes

Reaction equation

HRID 551924 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[CH:12])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].Br[C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1>C(#N)C.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>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 12081Methyl 4-bromobenzoateHCID 27751321-Butyl-4-ethynylbenzene

Product 1

HCID 57554541Methyl 4-[(4-butylphenyl)ethynyl]benzoateYield 55%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 1-butyl-4-ethynylbenzene (Aldrich, 25.0 g, 0.157 mol) and methyl 4-bromobenzoate (Aldrich, 30.9 g, 0.143 mol) in dry acetonitrile (300 mL) under nitrogen was added cuprous iodide (1.36 g, 7.18 mmol), TEA (43.6 g, 0.431 mol) followed by Pd(PPh3)2Cl2 (5.0 g, 7.18 mmol) and the reaction mixture was stirred at 85° C. for 20 hrs. The solvent was removed under reduced pressure. The residue was taken up with Et2O (300 ml) and washed with water and brine. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. Purification by flash chromatography on silicagel (PetEther) gave 23.0 g (55%) of the.title compound.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customPurification by flash chromatography on silicagel (PetEther)

Sources & evidence

ORD record
ord-d657b532b5234adfb8766aee28994fc0
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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