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

HRID 982918Notes

Reaction equation

HRID 982918 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][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+]>C(#N)C>[CH2:12]([O:11][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])[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 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

157 g (1.00 mol) of 3-fluoro-6-nitrophenol are initially taken in 500 ml of acetonitrile in a three-necked flask (KPG stirrer, reflux condenser, inert gas connection), and 174 g (1.02 mol) of benzyl bromide and 345 g (2.50 mol) of potassium carbonate are added in this sequence under inert gas. The mixture is refluxed for 3 hours at 90° C. After cooling to room temperature, the mixture is filtered with suction and the remaining solid is rinsed twice with 100 ml of acetonitrile each time. The solution is evaporated down until it crystallizes, and the crude product is filtered off with suction. The crude product is dissolved at room temperature in ethyl acetate (1 ml/g of crude product) and precipitated with hexane (3.6 ml/g of crude product). The mixture is stored overnight at T<−10° C. for complete crystallization.

Workup

  1. additionare added in this sequence under inert gas
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture is filtered with suction
  4. washthe remaining solid is rinsed twice with 100 ml of acetonitrile each time
  5. customThe solution is evaporated down until it
  6. customcrystallizes
  7. filtrationthe crude product is filtered off with suction
  8. dissolutionThe crude product is dissolved at room temperature in ethyl acetate (1 ml/g of crude product)
  9. customprecipitated with hexane (3.6 ml/g of crude product)
  10. customThe mixture is stored overnight at T<−10° C. for complete crystallization

Sources & evidence

ORD record
ord-245e4327089745989013964c8a5dd65d
Source dataset
uspto-grants-2005_03
Patent number
US06861560B2

Reaction notes

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