Cesium carbonate → 2'-Chloro-5'-nitro-biphenyl-4-carboxylic acid ethyl ester

HRID 1678485Notes

Reaction equation

HRID 1678485 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[Cl:11].[CH2:12]([O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)=[O:16])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[CH2:12]([O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=2[Cl:11])=[CH:19][CH:18]=1)=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27343504-Ethoxycarbonylphenylboronic acidHCID 27355492-Bromo-1-chloro-4-nitrobenzene

Product 1

HCID 598223932'-Chloro-5'-nitro-biphenyl-4-carboxylic acid ethyl esterYield 93.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-bromo-1-chloro-4-nitro-benzene (2.5 g), 4-ethoxycarbonyl-phenyl boronic acid (2.05 g), cesium carbonate (3.44 g) and tetrakis(triphenylphosphine)palladium0 (catalytic quantity), in 1:2 aqueous DME (45 ml) was heated to reflux for 18 h. The mixture was then cooled and partitioned between water and ethyl acetate. The dried extracts were evaporated to give the product as a white solid (3.01 g). This material was used in the next stage without further purification.

Workup

  1. temperatureto reflux for 18 h
  2. temperatureThe mixture was then cooled
  3. custompartitioned between water and ethyl acetate
  4. customThe dried extracts were evaporated

Sources & evidence

ORD record
ord-6977cb31729b42ff827e4ed78aace1e2
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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