Diphosgene → HCID 19082732, compound

HRID 963766Notes

Reaction equation

HRID 963766 reaction equation
[Cl:1][C:2]([O:4][C:5](Cl)(Cl)Cl)=[O:3].[CH3:9][O:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([CH2:19]CO)=[C:13]([N+:22]([O-:24])=[O:23])[CH:12]=1>C1COCC1>[CH3:9][O:10][C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([CH2:19][CH2:5][O:4][C:2]([Cl:1])=[O:3])=[C:13]([N+:22]([O-:24])=[O:23])[CH:12]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 13895882HCID 13895882, compound

Product 1

HCID 19082732HCID 19082732, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Trichloromethyl chloroformate (0.26 ml, 2.2 mmol) in THF (5 ml, dist. over CaH2) was cooled by means of an ice bath to 0° C. A solution of 2-(4,5-dimethoxy-2-nitrophenyl)ethanol (500 mg, 2.2 mmol) and Et3 N (218 mg, 0.3 ml, 2.2 mmol, dist. over CaH2) in THF (15 ml, dist. over CaH2) was added dropwise thereto for 10 min. The ice bath was then removed and the solution was stirred further at room temperature. After being stirred for 30 min, a spatula tip of activated carbon was added to the reaction mixture, which after being stirred for another 2.5 h was filtered by suction at room temperature over Celite. The solvent and the excess reagent were removed from the filtrate by distillation in a high vacuum and 2-(4,5-dimethoxy-2-nitrophenyl)ethoxycarbonyl chloride (624 mg, 98%) was obtained as a yellow brown solid.

Workup

  1. customThe ice bath was then removed
  2. stirringAfter being stirred for 30 min
  3. additiona spatula tip of activated carbon was added to the reaction mixture, which
  4. stirringafter being stirred for another 2.5 h
  5. filtrationwas filtered by suction at room temperature over Celite
  6. customThe solvent and the excess reagent were removed from the filtrate by distillation in a high vacuum

Sources & evidence

ORD record
ord-9fa9d24cc8a945329ee8e43aa223004d
Source dataset
uspto-grants-1998_06
Patent number
US05763599

Reaction notes

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