Water → HCID 58603321, compound

HRID 502647Notes

Reaction equation

HRID 502647 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.Cl.Cl[CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[C:4]([F:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 58603321HCID 58603321, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-2-fluorophenol (1.0 g, 5.24 mmol), 2-chloro-N,N-diethylethanamine HCL (0.90 mg, 5.24 mmol) and Cs2CO3 (8 g, 25 mmol) were combined in DMF (20 mL) and the mixture was heated at reflux over night. H2O was added and the mixture was extracted with EtOAc, then washed with 2N NaOH and brine. The organic layers were combined, dried over Na2SO4 and concentrated to a brown oil. Flash chromatography (gradient eluent: 10-50% EtOAc in hexanes) of the crude concentrate afforded title compound 56.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux over night
  3. extractionthe mixture was extracted with EtOAc
  4. washwashed with 2N NaOH and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a brown oil
  7. concentrationFlash chromatography (gradient eluent: 10-50% EtOAc in hexanes) of the crude concentrate

Sources & evidence

ORD record
ord-8d0813b43cb846e5a6e0b138a16b4852
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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