Benzyl Bromide → 1-Benzyloxy-4-bromo-2,5-difluorobenzene
Reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[C:18]1([CH2:17][O:9][C:5]2[CH:6]=[C:7]([F:8])[C:2]([Br:1])=[CH:3][C:4]=2[F:10])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4-bromo-2,5-difluorophenol (2 g, 9.57 mmol) was dissolved in DMF (19 mL) and to this was added Cs2CO3 (4.37 g, 13.34 mmol) and the solution was stirred for 15 minutes before benzyl bromide (1.64 g, 9.57 mmol) was added. After 1 hour at room temperature the mixture was partitioned between ethyl acetate (100 mL)/water (100 mL), the layers were separated and the aqueous extracted with ethyl acetate. The combined organics were washed with saturated NH4Cl (100 mL), water (100 mL) and brine (2×100 mL) and dried over MgSO4. The crude material (2.74 g) was filtered through a pad of silica and eluted with 20% Et2O in hexane to afford 4-bromo-2,5-difluorophenyl phenylmethyl ether after evaporation of the solvent (2.51 g, 88%).
Workup
- additionwas added
- customAfter 1 hour at room temperature the mixture was partitioned between ethyl acetate (100 mL)/water (100 mL)
- customthe layers were separated
- extractionthe aqueous extracted with ethyl acetate
- washThe combined organics were washed with saturated NH4Cl (100 mL), water (100 mL) and brine (2×100 mL)
- dry with materialdried over MgSO4
- filtrationThe crude material (2.74 g) was filtered through a pad of silica
- washeluted with 20% Et2O in hexane
Sources & evidence
- ORD record
- ord-f30b820de2864320a822d1a79833b6db
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07956083B2
Reaction notes
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