Methyl iodide → Methyl 3-bromo-4-(pyrrolidin-1-ylcarbonyl)benzoate

HRID 2053762Notes

Reaction equation

HRID 2053762 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:5]([OH:7])=[O:6].[C:18](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:5]([O:7][CH3:18])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 693124883-Bromo-4-(pyrrolidin-1-ylcarbonyl)benzoic acid

Product 1

HCID 69312594Methyl 3-bromo-4-(pyrrolidin-1-ylcarbonyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 g (67.1 mmol) of 3-bromo-4-(pyrrolidin-1-ylcarbonyl)benzoic acid is dissolved in 400 mL of N,N-dimethylformamide and combined with 21.9 g (67.1 mmol) cesium carbonate with stirring. Then 4.21 mL (67.1 mmol) of iodomethane is slowly added dropwise at ambient temperature and the mixture is stirred for 16 hours at ambient temperature. After the solid constituents have been removed by filtration with suction, volatile constituents are removed in vacuo. Yield: 20.94 g (75%); Rf value: 0.42 (silica gel; dichloromethane/ethanol=98:2); C13H14BrNO3 (312.17); mass spectrum: (M+H)+=312/314 (bromine isotope).

Workup

  1. stirringthe mixture is stirred for 16 hours at ambient temperature
  2. customAfter the solid constituents have been removed by filtration with suction, volatile constituents
  3. customare removed in vacuo

Sources & evidence

ORD record
ord-1f631f885c4c4dd887240ea6ca9a1da1
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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