Cesium fluoride → HCID 66761816, compound

HRID 561801Notes

Reaction equation

HRID 561801 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:21])[C:5]([Cl:20])=[C:6]([CH:19]=1)[CH2:7][N:8]([CH:16]1[CH2:18][CH2:17]1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[F-].[Cs+].[CH2:24]([Sn](CCCC)(CCCC)CCCC)[CH:25]=[CH2:26]>C1COCC1>[CH2:26]([C:2]1[CH:3]=[C:4]([Cl:21])[C:5]([Cl:20])=[C:6]([CH:19]=1)[CH2:7][N:8]([CH:16]1[CH2:18][CH2:17]1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:25]=[CH2:24]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 90628AllyltributylstannaneHCID 66761642HCID 66761642, compound

Product 1

HCID 66761816HCID 66761816, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF solution (0.12 M) of tert-butyl (5-bromo-2,3-dichlorobenzyl)cyclopropylcarbamate from the previous step (1 eq.), Pd(PCy3)2 (0.05 eq.) and cesium fluoride (2.0 eq.) was added allyl tributylstannane (1.2 eq.). The resulting brown solution was heated at reflux for 8 h and then filtered through a pad of SiO2. The insolubles were rinsed further with ether and the filtrate was concentrated in vacuo to afford a brown semisolid. Purification of the crude product thus obtained by way of column chromatography (SiO2, Hex→90:10 (v/v) Hex:Et2O) afforded the title compound as a pale yellow oil.

Workup

  1. temperatureThe resulting brown solution was heated
  2. temperatureat reflux for 8 h
  3. filtrationfiltered through a pad of SiO2
  4. washThe insolubles were rinsed further with ether
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto afford a brown semisolid
  7. customPurification of the crude product
  8. customthus obtained by way of column chromatography (SiO2, Hex→90:10 (v/v) Hex:Et2O)

Sources & evidence

ORD record
ord-27fe5bf243b64106b760fe6a94fb8caf
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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