Sodium Carbonate → Methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate

HRID 1935953Notes

Reaction equation

HRID 1935953 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([O-])=O)=[CH:13][CH:12]=2)=[CH:5][C:4]=1[CH:20]([CH3:22])[CH3:21].[C:23](N1C=CN=C1)(=O)C.[C:31]([O-:34])([O-])=[O:32].[Na+].[Na+]>CC#N.O>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:19]=[CH:18][C:14]([CH2:15][C:31]([O:34][CH3:23])=[O:32])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 22568806HCID 22568806, compound2×

Product 1

HCID 86585936Methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetateYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl]-benzoate (Intermediate 155, 120.0 mg, 0.31 mmol) and 1-acetylimidazole (36.0 mg, 0.33 mmol) in 5 mL CH3CN was heated at 65° C. for 4 hours and then at 55° C. for 16 hours. The solution was cooled to room temperature, diluted with H2O and made basic by addition of Na2CO3, and extracted with EtOAc. The combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4), and concentrated under reduced pressure. Column chromatography (1% Et3N in 5% MeOH-EtOAc) afforded 75.0 mg (65%) of the title compound as a colorless solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with H2O and saturated aqueous NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-63938cda97644b3a929a71659e3fbf9e
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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