Cesium carbonate → HCID 89704896, compound

HRID 1481337Notes

Reaction equation

HRID 1481337 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+].[C:18]([O:21][CH2:22][CH2:23]Br)(=[O:20])[CH3:19]>CN(C=O)C.CCOC(C)=O>[C:18]([O:21][CH2:22][CH2:23][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:20])[CH3:19]

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 solution 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-bromoethyl acetate (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 combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept/EtOAc (4/1) to EtOAc gives the desired compound as beige solid.

Workup

  1. washwashed 3 times with water
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification with CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-0ff5903f7ed74a6498d51455408d3879
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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