Pyrrolidine → 1-(2-Bromo-3-methylbenzoyl)pyrrolidine

HRID 1028935

Reaction equation

HRID 1028935 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:6]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 27355882-Bromo-3-methylbenzoic acid

Product 1

HCID 665791491-(2-Bromo-3-methylbenzoyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-3-methylbenzoic acid (5.0 g, 23.3 mmol) was dissolved in THF (100 mL) and added N,N′-carbonyldiimidazole (4.52 g, 27.9 mmol). The reaction mixture was stirred at ambient temperature for 14 h. Pyrrolidine (6.8 mL, 81 mmol) was added in one portion. The mixture was stirred for 8 h and then partitioned between EtOAc and water. The organic layer was washed with water, diluted HCl, saturated bicarbonate, water and brine. The solution was then concentrated in vacuo to afford (2-bromo-3-methylphenyl)(pyrrolidin-1-yl)methanone as a white crystalline solid, upon standing overnight at RT.

Workup

  1. stirringThe mixture was stirred for 8 h
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with water, diluted HCl, saturated bicarbonate, water and brine
  4. concentrationThe solution was then concentrated in vacuo

Sources & evidence

ORD record
ord-a11937687535417686898b6081575465
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Linked notes

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