Triethylamine → 2-(2-Nitrophenyl)propyl chloroformate

HRID 963767Notes

Reaction equation

HRID 963767 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([CH3:13])[CH2:11][OH:12])([O-:3])=[O:2].CCN(CC)CC.[Cl:21][C:22](OC(Cl)(Cl)Cl)=[O:23]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([CH3:13])[CH2:11][O:12][C:22]([Cl:21])=[O:23])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 113897552-(2-Nitrophenyl)propan-1-ol

Product 1

HCID 114479052-(2-Nitrophenyl)propyl chloroformateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(2-nitrophenyl)propanol (500 mg, 2.76 mmol) and Et3N (279 mg, 0.385 ml, 2.76 mmol, dist. over KOH) in THF (6.75 ml, dist. over CaH2) was dropped into a solution, cooled to 0° C., of trichloromethyl chloroformate (655 mg, 3.3 mmol) in THF (6.75 ml, see above). It was stirred for 1 h while being cooled in an ice bath and stirred for 1 h at room temperature. The mixture was filtered over Celite. Rewashing the filter cake with THF and removing the solvent and excess reagent from the pooled filtrates by distillation at 30° C. in a high vacuum yielded 2-(2-nitrophenyl)propoxycarbonyl chloride (644 mg, 96%) as a light brown oil.

Workup

  1. temperaturewhile being cooled in an ice bath
  2. stirringstirred for 1 h at room temperature
  3. filtrationThe mixture was filtered over Celite
  4. customremoving the solvent and excess reagent from the pooled filtrates
  5. distillationby distillation at 30° C. in a high vacuum

Sources & evidence

ORD record
ord-94e9fe9778a14ec7a2e4af1ba333de0d
Source dataset
uspto-grants-1998_06
Patent number
US05763599

Reaction notes

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