Triethylamine → HCID 19082703, compound

HRID 963764Notes

Reaction equation

HRID 963764 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH2:12][CH2:13][OH:14].CCN(CC)CC.[Cl:22][C:23](OC(Cl)(Cl)Cl)=[O:24]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH2:12][CH2:13][O:14][C:23]([Cl:22])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 19082707HCID 19082707, compound

Product 1

HCID 19082703HCID 19082703, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

For 5 min, a solution of 2-(2,4-dichloro-6-nitrophenyl)ethanol (500 mg, 2.12 mmol) and Et3N (214 mg, 2.12 mmol, dist. over KOH) in THF (5 ml, dist. over CaH2) was dropped into a solution, cooled to 0° C., of trichloromethyl chloroformate (503 mg, 2.5 mmol) in THF (5 ml, see above). It was stirred for 1 h while being cooled in an ice bath and stirred for 2 h at room temperature. The mixture was then 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-(2,4-dichloro-6-nitrophenyl)ethoxycarbonyl chloride (597 mg, 94%) as a bright yellow solid.

Workup

  1. temperaturewhile being cooled in an ice bath
  2. stirringstirred for 2 h at room temperature
  3. filtrationThe mixture was then 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-083074ba94544607b13d24c04f9b1e5e
Source dataset
uspto-grants-1998_06
Patent number
US05763599

Reaction notes

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