Dichloromethane → HCID 54494964, compound

HRID 1359326Notes

Reaction equation

HRID 1359326 reaction equation
C([O:8][C:9]1[C:10]([CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)C1C=CC=CC=1.ClCCl.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCCl>[OH:8][C:9]1[C:10]([CH:16]=[CH:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 69760052HCID 69760052, compound

Product 1

HCID 54494964HCID 54494964, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

875 mg of 3-benzyloxy-6-methyl-2-styrylpyridine (Example 57a) was dissolved in 15 ml of 1,2-dichloroethane and 1.2 ml of a dichloromethane solution containing 1.0 mol of boron tribromide was added thereto in a nitrogen atmosphere, followed by heating under stirring at 50° C. in an oil bath over night. After cooling as it was, an aqueous saturated sodium bicarbonate solution was added thereto, and the mixture was extracted with 5% methanol/dichloromethane. The organic phase was further washed with brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was vacuum-dried, to give 200 mg of the target compound.

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureAfter cooling as it
  4. extractionthe mixture was extracted with 5% methanol/dichloromethane
  5. washThe organic phase was further washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed
  8. customThe residue was vacuum-dried

Sources & evidence

ORD record
ord-29890e96ce7d4ebda794890e80f32bdc
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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