2,5-Dioxopyrrolidin-1-yl 4-bromo-2-chlorobenzoate → 1-[[2-Chloro-4-(tributylstannyl)benzoyl]oxy]-2,5-pyrrolidinedione

HRID 2270873Notes

Reaction equation

HRID 2270873 reaction equation
C([Sn](CCCC)(CCCC)[Sn](CCCC)(CCCC)CCCC)CCC.[Cl:27][C:28]1[CH:43]=[C:42]([Sn:44]([CH2:53][CH2:54][CH2:55][CH3:56])([CH2:49][CH2:50][CH2:51][CH3:52])[CH2:45][CH2:46][CH2:47][CH3:48])[CH:41]=[CH:40][C:29]=1[C:30]([O:32][N:33]1[C:37](=[O:38])[CH2:36][CH2:35][C:34]1=[O:39])=[O:31].BrC1C=CC(C(ON2C(=O)CCC2=O)=O)=C(Cl)C=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:27][C:28]1[CH:43]=[C:42]([Sn:44]([CH2:49][CH2:50][CH2:51][CH3:52])([CH2:53][CH2:54][CH2:55][CH3:56])[CH2:45][CH2:46][CH2:47][CH3:48])[CH:41]=[CH:40][C:29]=1[C:30]([O:32][N:33]1[C:37](=[O:38])[CH2:36][CH2:35][C:34]1=[O:39])=[O:31]

Participants

5

Reactant 2

HCID 159086832,5-Dioxopyrrolidin-1-yl 4-bromo-2-chlorobenzoateHCID 178448239HCID 178448239, compound

Product 1

HCID 159086841-[[2-Chloro-4-(tributylstannyl)benzoyl]oxy]-2,5-pyrrolidinedioneYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

1-[[2-Chloro-4-(tributylstannyl)benzoyl]oxy]-2,5-pyrrolidinedione Hexabutyldistannane (3.9 mL, 7.7 mmol) and tetrakis(triphenylphosphine)palladium(0) (103 mg, 0.09 mmol) were added to a solution of 1-[(4-bromo-2-chlorobenzoyl)oxy]-2,5-pyrrolidinedione (1.78 g, 5.4 mmol) in toluene (50 mL), and the solution was stirred at reflux for 6 h. The solvent was removed under reduced presure, and the oily residue was loaded onto a short plug of SiO2, washed with hexane, then eluted with 30% ethyl acetate hexanes. The solvent was evaporated and the residue was chromotagraphed (30% % ethyl acetate hexane) to give 1-[[2-chloro-4-(tributylstannyl)benzoyl]oxy]-2,5-pyrrolidinedione (1.74 g, 60%) as a colorless oil.

Workup

  1. temperatureat reflux for 6 h
  2. customThe solvent was removed
  3. washwashed with hexane
  4. washeluted with 30% ethyl acetate hexanes
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-891f731bc42844cc8fd7707380c052b8
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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