Benzyl Bromide → 1-Benzyloxy-4-bromo-2-fluoro-5-nitrobenzene

HRID 2421228Notes

Reaction equation

HRID 2421228 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([OH:11])=[C:4]([F:12])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([O:11][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 179763164-Bromo-2-fluoro-5-nitrophenol

Product 1

HCID 583039441-Benzyloxy-4-bromo-2-fluoro-5-nitrobenzeneYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromo-2-fluoro-5-nitrophenol (prepared according to WO2004/014361, 10 g, 42.3 mmol) and cesium carbonate (16.42 g, 50.4 mmol) in DMF (80 mL), was stirred at room temperature and treated with benzyl bromide (5.5 g, 46.5 mmol) and the mixture was stirred/sonicated at room temperature for 2 hours (˜30 mins sonication). The DMF was evaporated and water and ethyl acetate were added and the product was extracted into ethyl acetate. The combined extracts were washed with sodium bicarbonate solution, dried (Na2SO4) and concentrated. Trituration of the solid with diethyl ether (3×) and drying gave the title compound (D4), (12.50 g).

Workup

  1. customthe mixture was stirred/sonicated at room temperature for 2 hours
  2. custom(˜30 mins sonication)
  3. customThe DMF was evaporated
  4. additionwater and ethyl acetate were added
  5. extractionthe product was extracted into ethyl acetate
  6. washThe combined extracts were washed with sodium bicarbonate solution
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. dry with materialTrituration of the solid with diethyl ether (3×) and drying

Sources & evidence

ORD record
ord-355eac88103a42df86ced51d502ea8af
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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