Phenol → HCID 89581335, compound

HRID 1501254Notes

Reaction equation

HRID 1501254 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([CH:2]([O:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]([O:5][CH3:6])=[O:4])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 12717577Methyl bromo(4-bromophenyl)acetate

Product 1

HCID 89581335HCID 89581335, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 2-bromo-2-(4-bromophenyl)acetate (9 g, 29.3 mmol) in N,N-dimethylformamide was added phenol (5.5 g, 60 mmol), cesium carbonate (9.5 g, 30 mmol), tetrabutylammonium iodide (1.08 g, 2.93 mmol). The mixture was stirred at 40° C. for 15 hours. Thin layer chromatography showed the start material was consumed completely. Then the mixture was concentrated under vacuum and purified by column chromatography (silica gel, petroleum ether/ethyl acetate=25:1) to give methyl 2-(4-bromophenyl)-2-phenoxyacetate (6 g, 61%).

Workup

  1. customwas consumed completely
  2. concentrationThen the mixture was concentrated under vacuum
  3. custompurified by column chromatography (silica gel, petroleum ether/ethyl acetate=25:1)

Sources & evidence

ORD record
ord-1acb0abf186a44139be4c8db387d4bea
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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