4-Fluorobenzenesulfonyl chloride → 4-Fluorobenzene-1-sulfonyl azide

HRID 601602Notes

Reaction equation

HRID 601602 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N-:12]=[N+:13]=[N-:14].[Na+]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:12]=[N+:13]=[N-:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 33557Sodium Azide

Product 1

HCID 152559014-Fluorobenzene-1-sulfonyl azide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Suspend 4-fluorobenzenesulfonyl chloride (0.500 g, 2.57 mmol) and sodium azide (0.200 g, 3.08 mmol) in acetone. Heat at reflux overnight before concentrating the reaction mixture. Purify by flash 40 chromatography, eluting with 10% ethyl acetate in hexanes to give the title compound: 1H NMR (DMSO-d6) δ 7.58 (tt, J=8.04, 2.02 Hz, 2H), 8.12 (td, 4.89, 1.96 Hz, 2H); HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 50-99% over 19 min], tR=16.5 min, 92.4% purity.

Workup

  1. temperatureHeat
  2. temperatureat reflux overnight
  3. concentrationbefore concentrating the reaction mixture
  4. customPurify by flash 40 chromatography
  5. washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3366a91487b94c2a9590e76d88604955
Source dataset
uspto-grants-2011_03
Patent number
US07902372B2

Reaction notes

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