1-(Trimethylsilyl)pyrrolidin-2-one → 1-(4'-Bromophenoxycarbonyl)-2-pyrrolidinone

HRID 847222

Reaction equation

HRID 847222 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:3].C[Si](C)(C)[N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19]>C1C=CC=CC=1>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])=[O:3])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 844611-(Trimethylsilyl)pyrrolidin-2-oneHCID 52377364-Bromophenyl chloroformate

Product 1

HCID 197515271-(4'-Bromophenoxycarbonyl)-2-pyrrolidinoneYield 53%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 4-bromophenyl chloroformate (4.19 g, 20.0 mmol) in anhydrous benzene (20 ml) was added a solution of 1-trimethylsilyl-2-pyrrolidinone (3.46 g, 22.0 mmol) in anhydrous benzene (10 ml). The mixture was stirred at room temperature for 30 min. The reaction mixture was evaporated under reduced pressure to dryness to give a solid material. Recrystallization from 2-propanol afforded 3.00 g of colorless prisms. Yield 53%

Workup

  1. customThe reaction mixture was evaporated under reduced pressure to dryness
  2. customto give a solid material
  3. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-84b29e23496146fe8a04e42fd72c8965
Source dataset
uspto-grants-1992_08
Patent number
US05140041

Linked notes

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