Triethylamine → HCID 19082717, compound

HRID 963757Notes

Reaction equation

HRID 963757 reaction equation
[Br: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>[Br: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 190827272-(2-Bromo-6-nitrophenyl)ethan-1-ol

Product 1

HCID 19082717HCID 19082717, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(2-bromo-6-nitrophenyl)ethanol (500 mg, 2.03 mmol) and Et3N (206 mg, 2.03 mmol, dist. over KOH) in THF (5 ml, dist. over CaH2) was dropped into a solution, cooled to 0° C., of trichloromethyl chloroformate (442 mg, 2.23 mmol) in THF (5 ml, see above) for 10 min. It was stirred for 5 min while being cooled in an ice bath and for 1 h 45 min at room temperature. The mixture was filtered over Celite. Rewashing the filter cake with THF and removing the solvent and the excess reagent from the pooled filtrates by distillation at 30° C. in a high vacuum yielded 2-(2-bromo-6-nitrophenyl)ethoxycarbonyl chloride (625 mg, 99.8%) as a light brown oil.

Workup

  1. filtrationThe mixture was filtered over Celite
  2. customremoving the solvent
  3. distillationthe excess reagent from the pooled filtrates by distillation at 30° C. in a high vacuum

Sources & evidence

ORD record
ord-32f4fc01b99b4b77a804e6cbd17e966d
Source dataset
uspto-grants-1998_06
Patent number
US05763599

Reaction notes

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