Cesium carbonate → HCID 57467470, compound

HRID 1890796Notes

Reaction equation

HRID 1890796 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.Br[C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:4]([F:9])[CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 1819754-Chloro-2-fluorophenol

Product 1

HCID 57467470HCID 57467470, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 4-chloro-2-fluorophenol (11.280 g, 77 mmol), ethyl 2-bromoisobutyrate (12.61 mL, 85 mmol) and cesium carbonate (37.6 g, 115 mmol) in N,N-dimethylformamide (100 mL) was stirred at 55° C. for 18 hours. The reaction mixture was poured into brine, and extracted with ethyl acetate (2×250 mL). The combined organic phases were washed with brine, dried (MgSO4) and concentrated. The crude product was used in the next step without additional purification. MS (DCI+) m/z 278 (M+NH4)+.

Workup

  1. extractionextracted with ethyl acetate (2×250 mL)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was used in the next step without additional purification

Sources & evidence

ORD record
ord-412d1c0508c4432d8f97325842cacaf6
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

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