Water → 2-Allyloxy-2',6'-dichloro-biphenyl

HRID 902300Notes

Reaction equation

HRID 902300 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:10]([OH:15])=[CH:11][CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH:23]=[CH2:24].O>CC(C)=O>[CH2:24]([O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8])[CH:23]=[CH2:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 689645942',6'-Dichlorobiphenyl-2-ol

Product 1

HCID 691169382-Allyloxy-2',6'-dichloro-biphenylYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2′,6′-dichloro-1,1′-biphenyl-2-ol (5.4 g, 0.0226 mol) in acetone (100 mL) was added potassium carbonate (3.75 g, 0.0271 mol) followed by allyl bromide (2.58 mL, 0.0298 mol) and the reaction mixture heated to reflux for 24 hours. The cooled reaction mixture was poured into water (300 mL), the mixture stirred vigorously for 1 hour then extracted with ethyl acetate (300 mL). The separated organic extract was washed with water (200 mL) and saturated brine (200 mL), dried over magnesium sulfate and concentrated under reduced pressure to afford a yellow syrup. Purification by flash chromatography using a solvent gradient of 1 to 2% ethyl acetate in hexane gave 5.84 g (93%) of 2′-(allyloxy)-2,6-dichloro-1,1′-biphenyl as a colorless oil. MS (EI) m/z 278 (M+).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 24 hours
  3. customThe cooled reaction mixture
  4. extractionthen extracted with ethyl acetate (300 mL)
  5. extractionThe separated organic extract
  6. washwas washed with water (200 mL) and saturated brine (200 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto afford a yellow syrup
  10. customPurification by flash chromatography

Sources & evidence

ORD record
ord-968737e19c144d2e886145586bd2539f
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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