Trichloroacetyl chloride → HCID 59432914, compound

HRID 576049Notes

Reaction equation

HRID 576049 reaction equation
C(N(CC)CC)C.[CH2:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][NH:9]1.[Cl:17][C:18]([Cl:23])([Cl:22])[C:19](Cl)=[O:20]>C(Cl)(Cl)Cl>[Cl:17][C:18]([Cl:23])([Cl:22])[C:19]([N:9]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8]1)=[O:20]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 422478Isoindoline

Product 1

HCID 59432914HCID 59432914, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (3.48 mL, 25.0 mmol) was added to a solution of isoindoline (4.98 g, 25.0 mmol) in chloroform (100 mL) at room temperature and the mixture was cooled in ice. Trichloroacetic acid chloride (2.79 mL, 25.0 mmol) was added dropwise thereto and the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to afford 2,2,2-trichloro-1-(1,3-dihydro-2 H-isoindol-2-yl)ethanone as a purple powder (6.59 g).

Workup

  1. temperaturethe mixture was cooled in ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-ab098ae7a6af4c4fa08c77fd9a7b99a8
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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