1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(1-Azidoethyl)-1chloro-2-(methylsulfonyl)benzene

HRID 1845145Notes

Reaction equation

HRID 1845145 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH3:9])=[CH:4][C:3]=1[S:11]([CH3:14])(=[O:13])=[O:12].C1(P([N:29]=[N+:30]=[N-:31])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:29]([CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:4]=1)[CH3:9])=[N+:30]=[N-:31]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 581879811-(4-Chloro-3-(methylsulfonyl)phenyl)ethanol

Product 1

HCID 581883824-(1-Azidoethyl)-1chloro-2-(methylsulfonyl)benzeneYield 28.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A round bottom flask was charged with 1-(4-chloro-3-(methylsulfonyl)phenyl)ethanol (8.5 g, 32.44 mmol) and toluene (100 mL). Diphenyl phosphoryl azide (8.4 mL, 38.93 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (5.8 mL, 38.93 mmol) were added at 0° C. and the mixture was stirred over night at room temperature. The volatiles were removed under reduced pressure and the residue was diluted with water and extracted with EtOAc. The combined organic layers were concentrated under reduced pressure and the residue was purified by column chromatography to get the product (2.4 g, 28% yield).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. concentrationThe combined organic layers were concentrated under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-31cfe15c171a4ee681b2e1935dc90c7c
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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