Sodium Chloride → HCID 15907506, compound

HRID 1883668Notes

Reaction equation

HRID 1883668 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([CH2:15][C:16]#[N:17])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.[Cl-].[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:10]([CH2:15][C:16]#[N:17])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 25134Boron tribromideHCID 23508412HCID 23508412, compound

Product 1

HCID 15907506HCID 15907506, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

89 mg of 4′-methoxy-2-biphenylacetonitrile was dissolved in 0.66 ml of methylene chloride, and 0.8 ml of a 1 M solution of boron tribromide in methylene chloride was added thereto under cooling with ice, followed by stirring for 40 minutes. This mixture was returned to room temperature and stirred for an additional 40 minutes. After the reaction mixture was poured into a saturated aqueous solution of sodium chloride, the product was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the resulting crude product was purified by TLC (using a 2:1 mixture of hexane and ethyl acetate as the developing solvent) to obtain 43 mg of 4′-hydroxy-2-biphenylacetonitrile.

Workup

  1. temperatureunder cooling with ice
  2. customwas returned to room temperature
  3. stirringstirred for an additional 40 minutes
  4. extractionthe product was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off
  8. customthe resulting crude product was purified by TLC (
  9. additiona 2:1 mixture of hexane and ethyl acetate as the developing solvent)

Sources & evidence

ORD record
ord-b546f780752c4faeb112f5eb6027e1b9
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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