Diethyl Ether → 2-(Benzyloxy)-4-fluoro-1-nitrobenzene

HRID 363296Notes

Reaction equation

HRID 363296 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+].CCOCC>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzeneYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-fluoro-2-nitrophenol (28 g, 0.178 mol), benzyl bromide (33.53 g, 0.195 mol) and K2CO3 (30.8 g, 0.223 mol) in anhydrous DMF (150 mL) was stirred at room temperature for 12 h. After the reaction was complete, the reaction mixture was poured into a mixture of ether (1000 mL) and water (200 mL). The organic phase was separated, washed with water (3×100 mL), dried (MgSO4) and concentrated to give the title compound of Step A (40.5 g).

Workup

  1. customThe organic phase was separated
  2. washwashed with water (3×100 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fb01a49c9f8843d3a752b13dc7903fb2
Source dataset
uspto-grants-1999_02
Patent number
US05874382

Reaction notes

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