Bromine → 4-Bromo-2-fluoroanisole

HRID 1761826Notes

Reaction equation

HRID 1761826 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Br:10]Br>C(Cl)(Cl)Cl>[Br:10][C:6]1[CH:5]=[CH:4][C:3]([O:8][CH3:9])=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 675762-Fluoroanisole

Product 1

HCID 753784-Bromo-2-fluoroanisoleYield 73.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Fluoroanisole (266 g) was dissolved in 700 ml of chloroform and 337 g of bromine was added dropwise to the solution. The mixture was reacted under reflux at 67° to 68° C. for 1 hour, subsequently left to cool, washed with a 5% aqueous solution of sodium hydroxide and then with water, and dried with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was distilled (95° to 96° C./12 mmHg) to obtain 317 g of 4-bromo-2-fluoroanisole (yield 73.4%).

Workup

  1. customThe mixture was reacted
  2. temperatureunder reflux at 67° to 68° C. for 1 hour
  3. waitsubsequently left
  4. temperatureto cool
  5. washwashed with a 5% aqueous solution of sodium hydroxide
  6. dry with materialwith water, and dried with anhydrous sodium sulfate
  7. distillationAfter the solvent was distilled off under reduced pressure
  8. distillationthe residue was distilled (95° to 96° C./12 mmHg)

Sources & evidence

ORD record
ord-869861fd4b0f4d459d2627340aecb75a
Source dataset
uspto-grants-1989_05
Patent number
US04828754

Reaction notes

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