Water → 1-(Allyloxy)-2-bromo-4-fluorobenzene

HRID 902307Notes

Reaction equation

HRID 902307 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[CH:17]=[CH2:18].O>CC(C)=O>[CH2:18]([O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Br:1])[CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 133575831-(Allyloxy)-2-bromo-4-fluorobenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-bromo-4-fluorophenol (9.75 g, 0.051 mol) and potassium carbonate (7.76 g, 0.056 mol) in acetone (125 mL) was added allyl bromide (4.64 mL, 0.054 mol) and the reaction mixture heated to reflux for 3.5 hours. The cooled reaction mixture was then poured into water and the resulting oily suspension extracted with dichloromethane (2×500 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford 11.79 g (100%) of 1-(allyloxy)-2-bromo-4-fluorobenzene as a yellow oil. MS (ESI) m/z 229.9 (M+).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 3.5 hours
  3. customThe cooled reaction mixture
  4. extractionthe resulting oily suspension extracted with dichloromethane (2×500 mL)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef161733786843a09009cb5341a41296
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

Loading…