Triphenylphosphine → HCID 59407586, compound

HRID 1093416Notes

Reaction equation

HRID 1093416 reaction equation
[C:1]1(=[O:14])[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH2:11][CH2:12]O)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>C(Cl)Cl>[Br:34][CH2:12][CH2:11][CH2:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[C:1](=[O:14])[CH2:2][CH2:3]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 59407593HCID 59407593, compound

Product 1

HCID 59407586HCID 59407586, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 56-2 (1.15 g) was dissolved in methylene chloride (20 ml), triphenylphosphine (1.74 g) and N-bromosuccinimide (1.18 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 2 hr, and further at room temperature for 15 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography to give the object product (430 mg) as a yellow oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. washThe reaction mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionDiethyl ether (100 ml) was added
  7. filtrationthe precipitated triphenylphosphine oxide was filtered off
  8. concentrationThe concentrate of the filtrate
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-217889fcae264bc191ee03a9cea9f249
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

Loading…