Cesium carbonate → (2-(5-Bromo-2-chlorophenoxy)ethyl)(methyl)sulfane

HRID 1013759Notes

Reaction equation

HRID 1013759 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.Cl[CH2:11][CH2:12][S:13][CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([CH:7]=1)[O:8][CH2:11][CH2:12][S:13][CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 109652-Chloroethyl methyl sulfideHCID 8203925-Bromo-2-chlorophenol

Product 1

HCID 67317126(2-(5-Bromo-2-chlorophenoxy)ethyl)(methyl)sulfane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-2-chlorophenol (500 mg, 2410 μmol) and (2-chloroethyl)(methyl)sulfane (262 μl, 2651 μmol) were combined with cesium carbonate (942 mg, 2892 μmol) in DMF and heated to 100° C. for 2 h. The mixture was then filtered and purified using reverse phase chromatography. This purified material was carried forward to the next step.

Workup

  1. filtrationThe mixture was then filtered
  2. custompurified

Sources & evidence

ORD record
ord-374cc58ec982410faab4e19eef416d91
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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