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

HRID 515046Notes

Reaction equation

HRID 515046 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-ab26131290954387bbb22d330acaca7e
Source dataset
uspto-grants-2015_08
Patent number
US09108948B2

Reaction notes

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