Methane, dichloromethoxy- → 5-Trichloroacetyl-1H-pyrrole-3-carbaldehyde

HRID 1093976Notes

Reaction equation

HRID 1093976 reaction equation
[Cl:1][C:2]([Cl:11])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[Al+3].[Cl-].[Cl-].[Cl-].Cl[CH:17](Cl)[O:18]C>C(Cl)Cl.[N+](C)([O-])=O>[Cl:11][C:2]([Cl:1])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[C:8]([CH:17]=[O:18])[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 21004Methane, dichloromethoxy-HCID 3214872-(Trichloroacetyl)pyrroleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 124599775-Trichloroacetyl-1H-pyrrole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 23431834Dichloromethane nitromethaneSolvent

Procedure

To a solution of the compound obtained in Step A (87 mmoles) and AlCl3 in a DCM/nitromethane mixture (80 ml/80 ml) there is added, dropwise, at −30° C., dichloro-methoxy-methane (130.5 mmoles). After stirring for two hours, the reaction mixture is poured into 800 ml of ice-cold water. The aqueous phase is extracted with AcOEt, and then the organic phases are combined. The organic phase is washed with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness to yield the title product (brown crystals), which is used directly in the next Step.

Workup

  1. customat −30° C.
  2. extractionThe aqueous phase is extracted with AcOEt
  3. washThe organic phase is washed with saturated aqueous NaCl solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-5e41a93ed1b04d8aa683669eed8cd766
Source dataset
uspto-grants-2012_03
Patent number
US08133889B2

Reaction notes

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