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

HRID 494443Notes

Reaction equation

HRID 494443 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.O.[I-]>[CH2:18]([O:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([F:1])[CH:7]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzeneYield 97%

Reagents, catalysts & solvents 3

HCID 30165Iodide IonCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-fluoro-4-hydroxynitrobenzene (5.08 g, 32.36 mmol), cesium carbonate (11.71 g, 36.24 mmol), benzyl bromide (4.31 mL, 36.24 mmol), and tetrabutylamunonium iodide (50 mg) in N,N-dimethylformamide (50 mL) was stirred at 25° C. for 24 hours, diluted with water (200 mL) and extracted with ethyl acetate (3×). The combined organic layers were washed with water (3×) and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (7.72 g, 97%). 1H NMR (300 MHz, CDCl3): δ 8.10 (m, 1 H), 7.40 (m, 5 H), 6.82 (m, 2 H), 5.15 (s, 2 H).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic layers were washed with water (3×) and saturated sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f070717d7d54180af8a8b512d3c55be
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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