Triethylamine → Methyl 3-(2-chloro-6-fluorophenyl)-2-diazo-3-oxopropionate

HRID 598152Notes

Reaction equation

HRID 598152 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9](=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12].C(N(CC)CC)C.CS([N:27]=[N+:28]=[N-])(=O)=O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9](=[O:15])[C:10](=[N+:27]=[N-:28])[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 556271Methanesulfonyl azideHCID 67267062Methyl 3-(2-chloro-6-fluorophenyl)-3-oxopropanoate

Product 1

HCID 86613890Methyl 3-(2-chloro-6-fluorophenyl)-2-diazo-3-oxopropionateYield 76.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5.80 g (25.1 mmol) of methyl 3-(2-chloro-6-fluorophenyl)-3-oxopropionate in 60 mL acetonitrile was added 3.9 mL (28 mmol) of triethylamine followed by 3.05 g (25.2 mmol) of methanesulfonyl azide. The mixture was stirred at room temperature for 18 h and concentrated by rotary evaporation. The resulting solid mass was washed with ethyl acetate/hexanes and the washings were filtered through a plug of silica gel. The filtrate was concentrated to give 4.90 g (76%) of the title compound as a light yellow solid.

Workup

  1. concentrationconcentrated by rotary evaporation
  2. washThe resulting solid mass was washed with ethyl acetate/hexanes
  3. filtrationthe washings were filtered through a plug of silica gel
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7b07f3751c3841798e0a6e2aecd0659a
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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