Allyl bromide → HCID 69117900, compound

HRID 902347Notes

Reaction equation

HRID 902347 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([OH:15])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH:23]=[CH2:24]>CN(C=O)C>[CH2:24]([O:15][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[CH:23]=[CH2:22]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 69117522HCID 69117522, compound

Product 1

HCID 69117900HCID 69117900, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-chloro-2′-methyl-biphenyl-2-ol (4.75 g, 21.7 mmol) in DMF (30 mL) was added potassium carbonate (4.5 g, 32.6 mmol) and allyl bromide (3.0 mL, 32.6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 4 h. The mixture was extracted with ethyl acetate, washed with water and saturated sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by ISCO using a solvent gradient of O to 30% ethyl acetate in hexanes provided 5.6 g (100%) of 2-allyloxy-6-chloro-2′-methylbiphenyl as a light yellow oil.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with water and saturated sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by ISCO

Sources & evidence

ORD record
ord-47b8d94b53c746d6ba50865ec79da874
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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