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

HRID 1042900Notes

Reaction equation

HRID 1042900 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-2aa2ff08953447e49fb9e6a08613eaf6
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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