Water → HCID 12132989, compound

HRID 1006433Notes

Reaction equation

HRID 1006433 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)[CH2:13][CH2:14]O)=[CH:8][CH:7]=1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:46].O>C(#N)C>[Br:46][CH2:14][CH2:13][CH:12]([C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:5])[N:3]([CH2:24][CH3:25])[CH2:1][CH3:2])=[CH:7][CH:8]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 12132988HCID 12132988, compound

Product 1

HCID 12132989HCID 12132989, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(4-Diethylcarbamoylphenyl)-1-hydroxy-3-(3-methoxyphenyl)propane (215 mg) was dissolved in acetonitrile (4 ml), added with triphenylphosphine (304 mg) and carbon tetrabromide (385 mg) under ice cooling and stirred at room temperature for 30 minutes. The reaction mixture was added with water (5 ml) and extracted twice with dichloromethane (5 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate=2:1) to obtain 189 mg of the title compound. Yield: 74%.

Workup

  1. extractionextracted twice with dichloromethane (5 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate=2:1)

Sources & evidence

ORD record
ord-f1ee65b5f6d14d0a9cacb8c742fd4fad
Source dataset
uspto-grants-2004_09
Patent number
US06790854B2

Reaction notes

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