Cesium carbonate → 1-Bromo-3-fluoro-5-propoxybenzene

HRID 20435Notes

Reaction equation

HRID 20435 reaction equation
[CH2:1](I)[CH2:2][CH3:3].[Br:5][C:6]1[CH:7]=[C:8]([OH:13])[CH:9]=[C:10]([F:12])[CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:5][C:6]1[CH:7]=[C:8]([O:13][CH2:1][CH2:2][CH3:3])[CH:9]=[C:10]([F:12])[CH:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 219046363-Bromo-5-fluorophenol

Product 1

HCID 685580051-Bromo-3-fluoro-5-propoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add propyl iodide (5.74 g, 33.77 mmol) to 3-bromo-5-fluoro-phenol (4.30 g, 22.51 mmol) and cesium carbonate (11.00 g, 33.77 mmol) in N,N-dimethylformamide (75 mL) and stir at room temperature 1 hour, then heat at 50° C. for 1 hour. Cool to room temperature and dilute with hexanes. Wash (water, 1N lithium chloride, saturated aqueous sodium chloride), dry (magnesium sulfate), filter and concentrate to give the desired compound as a colorless oil, 4.40 g (83.8%).

Workup

  1. temperatureheat at 50° C. for 1 hour
  2. temperatureCool to room temperature
  3. washWash (water, 1N lithium chloride, saturated aqueous sodium chloride)
  4. dry with materialdry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-eb96c5088f05479f886160d7fefef98d
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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