Benzyl Bromide → 4-Bromo-2,6-difluoro-1-(benzyloxy)benzene

HRID 2421245Notes

Reaction equation

HRID 2421245 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[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[C:6]([F:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[F:10])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 27362924-Bromo-2,6-difluorophenol

Product 1

HCID 142076414-Bromo-2,6-difluoro-1-(benzyloxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-bromo-2,6-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 2 hours 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 (100 mL). The combined organics were washed with brine (2×50 mL) and water (2×50 mL) and dried over MgSO4. The crude material (2.67 g) was filtered through a pad of silica and eluted with hexane to afford 4-bromo-2,6-difluorophenyl phenylmethyl ether after evaporation of the solvent (2.38 g, 83%).

Workup

  1. additionwas added
  2. customAfter 2 hours at room temperature the mixture was partitioned between ethyl acetate (100 mL)/water (100 mL)
  3. customthe layers were separated
  4. extractionthe aqueous extracted with ethyl acetate (100 mL)
  5. washThe combined organics were washed with brine (2×50 mL) and water (2×50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationThe crude material (2.67 g) was filtered through a pad of silica
  8. washeluted with hexane

Sources & evidence

ORD record
ord-8ba7c860194646019c0cda6636386edc
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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