Cesium carbonate → HCID 89704896, compound

HRID 1051942Notes

Reaction equation

HRID 1051942 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[C:8]([Cl:10])[CH:9]=1)[CH:6]=[O:7].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23]>CN(C=O)C.CCOC(C)=O>[C:22]([O:21][CH2:20][CH2:19][O:11][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[C:8]([Cl:10])[C:5]=1[CH:6]=[O:7])(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 5283902,4-Dichloro-6-hydroxybenzaldehyde

Product 1

HCID 89704896HCID 89704896, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a soln. of 4,6-dichlorosalicylaldehyde (3.72 mmol) in 5 mL DMF was added Cs2CO3 (3.72 mmol) followed by KI (3.72 mmol) and 2-bromoethylacetate (8.68 mmol). The reaction mixture was heated to 100° C. for 4 h and then stirred at RT for 3 days. The mixture was diluted with EtOAc and washed 3 times with water and then with brine. The comb. org. layers were dried over MgSO4 and conc. in vacuo. Purification with CC (20-100% EtOAc/Hept) gives the desired compound as beige solid.

Workup

  1. washwashed 3 times with water
  2. dry with materiallayers were dried over MgSO4 and conc. in vacuo
  3. customPurification with CC (20-100% EtOAc/Hept)

Sources & evidence

ORD record
ord-73b420a48f044466a28f58251bf72be8
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

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