Methanesulfonyl chloride → 2-(2-bromophenyl)-3-methyl-2H-azirine

HRID 475112Notes

Reaction equation

HRID 475112 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[N:11]O)[CH3:10].CS(Cl)(=O)=O.N12CCCN=C1CCCCC2>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:9]([CH3:10])=[N:11]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 866946991-(2-Bromophenyl)propan-2-one oxime

Product 1

HCID 712717232-(2-bromophenyl)-3-methyl-2H-azirine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(2-bromophenyl)propan-2-one oxime (1.36 g, 5.96 mmol) and TEA (722 mg, 7.15 mmol) in anhydrous THF (50 mL) at RT was added dropwise a solution of methanesulfonyl chloride (819 mg, 7.15 mmol) in anhydrous THF (5 mL). After stirring at RT for 1 h, 1,8-diazabicyclo[5.4.0]undec-7-ene (2.26 g, 14.9 mmol) was added and stirring continued at RT for 1 h. The reaction mixture was passed through a pad of SiO2, concentrated in vacuo, and purified by SiO2 chromatography eluting with petroleum ether/EtOAc (10:1) to afford 2-(2-bromophenyl)-3-methyl-2H-azirine as yellow oil (758 mg, yield, 60.5%). MS (ESI): m/z=242.1 [M+33]+.

Workup

  1. stirringstirring
  2. waitcontinued at RT for 1 h
  3. concentrationconcentrated in vacuo
  4. custompurified by SiO2 chromatography
  5. washeluting with petroleum ether/EtOAc (10:1)
  6. customto afford

Sources & evidence

ORD record
ord-49b66707e4f34fa0a84c784eb2e5410a
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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