Cesium carbonate → HCID 58528999, compound

HRID 1431002Notes

Reaction equation

HRID 1431002 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH:5]=1.I[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].S([O-])([O-])(=O)=O.[Mg+2].CC(=NO)C(C)=NO>C(#N)C.[Cu-]=O>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=[C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH:5]=1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 58528929HCID 58528929, compoundHCID 135459645Dimethylglyoxime

Product 1

HCID 58528999HCID 58528999, compoundYield 23.5%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(4-bromophenoxy)-5-hydroxybenzoic acid methyl ester (200 mg, 0.619 mmol) in 10 mL of acetonitrile was added iodobenzene (189 mg, 0.928 mmol), cesium carbonate (403 mg, 1.24 mmol), copper(I)oxide (5 mg, 0.03 mmol), magnesium sulfate (185 mg), and dimethylglyoxime (14 mg, 0.124 mmol). The mixture was stirred at reflux for 16 h. Then the mixture was filtered through a pad of Celite and the filtrate was evaporated. The residue was chromatographied on silica gel using an ethyl acetate-hexane gradient afforded 58 mg (23%) of 3-(4-bromophenoxy)-5-phenoxybenzoic acid methyl ester: 1H NMR (300 MHz, DMSO-d6) δ 3.79 (s, 3H), 7.00-7.02 (m, 1H), 7.08-7.18 (m, 6H), 7.20-7.26 (m, 1H), 7.43-7.46 (m, 2H), 7.61 (d, 2H, J=9 Hz).

Workup

  1. temperatureat reflux for 16 h
  2. filtrationThen the mixture was filtered through a pad of Celite
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-c24e74f4731b4ba0a7ed41d15024c610
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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