Cesium carbonate → HCID 59822345, compound

HRID 1678480Notes

Reaction equation

HRID 1678480 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[CH2:13]([O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[CH2:13]([O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=2[O:11][CH3:12])=[CH:20][CH:19]=1)=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 788702-Bromo-4-nitroanisoleHCID 27343504-Ethoxycarbonylphenylboronic acid

Product 1

HCID 59822345HCID 59822345, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-bromo-1-methoxy-4-nitro-benzene (1 g), 4-ethoxycarbonyl-phenyl boronic acid (836 mg), cesium carbonate (1.4 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 and the residue purified on silica gel. Elution with 5-40% ethyl acetate:petrol gave a yellow solid (997 mg).

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
  5. customthe residue purified on silica gel
  6. washElution with 5-40% ethyl acetate

Sources & evidence

ORD record
ord-5d97c8c3fab94f99b5388547b12690b5
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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