Bromobenzene → HCID 68505148, compound

HRID 1176574Notes

Reaction equation

HRID 1176574 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O1CCOCC1>ClCCl>[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]1=[O:7]

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 11029774(3S)-3-hydroxypyrrolidin-2-one

Product 1

HCID 68505148HCID 68505148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A Schlenk flask is initially charged with 0.123 g of 3(S)-hydroxy-pyrrolidin-2-one, 0.453 g of caesium carbonate, 0.032 g of dipalladiumtris(dibenzylidenacetone)-chloroform complex and 0.052 g of 9,9-dimethyl-4,5-bis(diphenylphosphine)xanthane under argon. 0.110 ml of bromobenzene and 2 ml dioxane are added and the reaction mixture is heated to reflux over 14 hours. The reaction mixture is subsequently cooled to room temperature, diluted with dichloromethane and filtered through Hyflo, and the filtrate is concentrated by evaporation. The title compound is obtained as a beige solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.24 (4:1 EtOAc-heptane); Rt=2.50.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux over 14 hours
  3. filtrationfiltered through Hyflo
  4. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-9f5fc15d8d59410c9117a235ce4cd8e5
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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