Triethylamine → 2-(2-Fluoro-6-nitrophenyl)ethoxycarbonyl chloride

HRID 963753Notes

Reaction equation

HRID 963753 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:11][CH2:12][OH:13].CCN(CC)CC.[Cl:21][C:22](OC(Cl)(Cl)Cl)=[O:23]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:11][CH2:12][O:13][C:22]([Cl:21])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 156914472-(2-Fluoro-6-nitrophenyl)ethan-1-ol

Product 1

HCID 190827042-(2-Fluoro-6-nitrophenyl)ethoxycarbonyl chlorideYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(2-fluoro-6-nitrophenyl)ethanol (500 mg, 2.7 mmol) and Et3N (273 mg, 2.7 mmol, dist. over KOH) in THF (6.75 ml, dist. over CaH2) was dropped into a solution, cooled to 0° C., of trichloromethyl chloroformate (641 mg, 3.24 mmol) in THF (6.75 ml, see above) for 5 min. It was stirred for 1 h while cooling in an ice bath and then 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-fluoro-6-nitrophenyl)ethoxycarbonyl chloride (620 mg, 93%) as a light-brown oil.

Workup

  1. temperaturewhile cooling 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-9d8eaa025efd4d009975cbe04a48523c
Source dataset
uspto-grants-1998_06
Patent number
US05763599

Reaction notes

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