Allyl bromide → HCID 21180843, compound

HRID 1386788Notes

Reaction equation

HRID 1386788 reaction equation
[F:1][C:2]1[CH:3]=[C:4](O)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH2:10](Br)[CH:11]=[CH2:12].C([O-])([O-])=[O:15].[K+].[K+]>CC(C)=O.O>[CH2:10]([C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[C:5]=1[OH:15])[CH:11]=[CH2:12]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 759283,5-Difluorophenol

Product 1

HCID 21180843HCID 21180843, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

3,5-difluorophenol (3.9 grams, 30 mmol), allyl bromide (3.4 mL, 39 mmol) and K2CO3 (12.4 grams, 90 mmol) were suspended in 75 mL acetone and the mixture was refluxed overnight. The mixture was diluted with water and extracted with EtOAc. The organic was dried over sodium sulfate and concentrated. 5.5 grams of crude allyl-3,5-difluorophenylether. The oil was heated to reflux for 6 h then cooled to room temperature. Flash chromatography (150 g silica, 1011 Hexane/EtOAc) afforded 5.2 grams (100%) of product. 1H NMR (400 MHz, CDCl3). δ 3.4 (d, 2H), 5.1-5.2 (m, 2H), 5.6 (s, 1H), 5.9-6.0 (m, 1H), 6.46.5 (m, 2H).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. extractionextracted with EtOAc
  3. dry with materialThe organic was dried over sodium sulfate
  4. concentrationconcentrated
  5. temperatureThe oil was heated
  6. temperatureto reflux for 6 h

Sources & evidence

ORD record
ord-4ffc8c7e1a5a44eeaf7e7a29f598853e
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

Loading…