Cesium carbonate → HCID 44570902, compound

HRID 508419Notes

Reaction equation

HRID 508419 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=1.[OH-].[Na+]>C(#N)C>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][C:11]([O:12][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=2)=[C:2]([Cl:1])[CH:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 5814364-(Bromomethyl)-1,2-difluorobenzene

Product 1

HCID 44570902HCID 44570902, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of methyl 3-chloro-4-hydroxybenzoate (comm, 6.48 g, 34.73 mmol) in acetonitrile was added cesium carbonate (28.29 g, 86.82 mmol) followed by 4-(bromomethyl)-1,2-difluorobenzene (comm, 10.78 g, 52.09 mmol). The reaction mixture was stirred at room temperature for 18 hours. A sodium hydroxide solution (0.5 M, 210 mL) was then added and the resulting white solid was collected by filtration to yield the title compound, which was used in the next step without further purification.

Workup

  1. filtrationthe resulting white solid was collected by filtration

Sources & evidence

ORD record
ord-f5b04f8e2e234ca9b20bade0717693d1
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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