Methyltriphenylphosphonium iodide → 1-Bromo-4-[(1S,2R)-2-vinylcyclopropyl]benzene

HRID 73298

Reaction equation

HRID 73298 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@@H:9]2[CH:11]=O)=[CH:4][CH:3]=1.[I-].[CH3:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@@H:9]2[CH:11]=[CH2:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 638159Methyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxideHCID 57515374trans-2-(4-Bromophenyl)cyclopropane-1-carbaldehyde

Product 1

HCID 684062521-Bromo-4-[(1S,2R)-2-vinylcyclopropyl]benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the aldehyde from Example 28C [(1S,2S)-2-(4-bromophenyl)cyclopropanecarbaldehyde] and methyltriphenylphosphonium iodide [CAS 2065-66-9] in anhydrous dichloromethane was stirred at 0° C. under N2. Potassium t-butoxide was added to this chilled mixture. The ice bath was removed and the mixture was stirred at room temperature for one hour. The mixture was quenched with saturated aqueous NH4Cl. The mixture was extracted with dichloromethane and the combined organic extracts were dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the residue was purified on silica gel with hexanes to provide the title compound.

Workup

  1. customThe ice bath was removed
  2. customThe mixture was quenched with saturated aqueous NH4Cl
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified on silica gel with hexanes

Sources & evidence

ORD record
ord-22bebeda1ff04931ad6b31b69223b022
Source dataset
uspto-grants-2014_09
Patent number
US08829041B2

Linked notes

Loading…