Benzyl Bromide → 2-(Benzyloxy)-4-fluoro-1-nitrobenzene

HRID 660826Notes

Reaction equation

HRID 660826 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:12]([O:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-fluoro-2-nitrophenol (1.57 g, 10 mmol) and benzyl bromide (1.25 mL, 10.5 mmol) in DMF (20 mL) is added K2CO3 (2.07 g, 15 mmol) and the suspension is stirred at RT overnight. The reaction is quenched with water and the aqueous layer is extracted with EtOAc. The combined organic layers are washed with water and brine, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure to give the product as a pale yellow solid.

Workup

  1. customThe reaction is quenched with water
  2. extractionthe aqueous layer is extracted with EtOAc
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-08a3af75e94b4a6dbf2045662035e984
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…