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Water → HCID 19688467, compound

HRID 1093434
Notes
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Reaction equation

HRID 1093434 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32]N1C(=O)CCC1=O.O>C(Cl)Cl>[Br:32][CH2:11][CH2:10][CH2:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 190752692,5-Dimethylbenzenepropanol

Product 1

HCID 19688467HCID 19688467, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

Compound 62-2 (1.64 g) was dissolved in methylene chloride (33 ml), triphenylphosphine (2.90 g) and N-bromosuccinimide (1.95 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 3.5 hr. Water was added to the reaction mixture, and the mixture was extracted with methylene chloride and washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone) to give the object product (1.97 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 3.5 hr
  3. extractionthe mixture was extracted with methylene chloride
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. additionDiethyl ether was added
  8. filtrationthe precipitated triphenylphosphine oxide was filtered off
  9. concentrationThe concentrate of the filtrate
  10. customwas purified by silica gel column chromatography (hexane alone)

Sources & evidence

ORD record
ord-6bfb7aea23ae4baaaf7dd43cd6cce673
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129361B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes