Allyl bromide → HCID 69117603, compound

HRID 902355Notes

Reaction equation

HRID 902355 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([OH:15])=[CH:10][CH:11]=[CH:12][C:13]=1[Cl:14].[H-].[Na+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C=O)C>[CH2:20]([O:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([Cl:14])[C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 69117513HCID 69117513, compound

Product 1

HCID 69117603HCID 69117603, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2′,6-dichloro-biphenyl-2-ol (10.0 g, 41.8 mmol) in DMF was added sodium hydride (60% in mineral oil, 2.5 g, 62.7 mmol) and allyl bromide (5.4 mL, 62.7 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. 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 0 to 30% ethyl acetate in hexanes provided 11.6 g (100%) of 2-allyloxv-2′,6-dichlorobiphenyl 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-5ffc28ee51ff4623851f5df2835db506
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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