Cesium carbonate → 1-Bromo-3-fluoro-5-propoxybenzene
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureheat at 50° C. for 1 hour
- temperatureCool to room temperature
- washWash (water, 1N lithium chloride, saturated aqueous sodium chloride)
- dry with materialdry (magnesium sulfate)
- filtrationfilter
- concentrationconcentrate
Sources & evidence
- ORD record
- ord-eb96c5088f05479f886160d7fefef98d
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745438B2
Reaction notes
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