Triethylamine → 2-(2,6-Dinitrophenyl)ethoxycarbonyl chloride

HRID 963750Notes

Reaction equation

HRID 963750 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][CH2:14][OH:15])([O-:3])=[O:2].CCN(CC)CC.[Cl:23][C:24](OC(Cl)(Cl)Cl)=[O:25]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][CH2:14][O:15][C:24]([Cl:23])=[O:25])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 108675832-(2,6-Dinitrophenyl)ethanol

Product 1

HCID 190827052-(2,6-Dinitrophenyl)ethoxycarbonyl chlorideYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(2,6-dinitrophenyl)ethanol (4.08 g, 19.23 mmol) and Et3N (2.7 ml, 19.28 mmol) in THF (30 ml, dist. over CaH2) was dropped in a solution, cooled to 0° C., of trichloromethyl chloroformate (3.81 g, 2.33 ml, 19.28 mmol) in THF (10 ml, see above) for 20 min. This solution was stirred for 25 min while cooling in an ice bath, and was then stirred for 1 h 45 min at room temperature. The mixture was filtered over Celite. Rewashing the filter cake with THF, removing the solvent and excess reagent from the pooled filtrates by distillation and drying in a high vacuum yielded 5.13 g 2-(2,6-dinitrophenyl)-ethoxycarbonyl chloride (97%) as a light-brown solid.

Workup

  1. temperaturewhile cooling in an ice bath
  2. stirringwas then stirred for 1 h 45 min at room temperature
  3. filtrationThe mixture was filtered over Celite
  4. customremoving the solvent and excess reagent from the pooled filtrates
  5. distillationby distillation
  6. customdrying in a high vacuum

Sources & evidence

ORD record
ord-791c3164c9eb486b8a01e2622374f8fc
Source dataset
uspto-grants-1998_06
Patent number
US05763599

Reaction notes

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