Trichloroacetyl chloride → HCID 68517068, compound

HRID 1948316Notes

Reaction equation

HRID 1948316 reaction equation
[F:1][C:2]1[C:6]([F:7])=[CH:5][NH:4][C:3]=1[CH3:8].C([O-])([O-])=O.[K+].[K+].[Cl:15][C:16]([Cl:21])([Cl:20])[C:17](Cl)=[O:18].C([O-])(O)=O.[Na+]>C(OCC)C.C(Cl)Cl.CCCCC>[Cl:15][C:16]([Cl:21])([Cl:20])[C:17]([C:5]1[NH:4][C:3]([CH3:8])=[C:2]([F:1])[C:6]=1[F:7])=[O:18]

Participants

8

Reactant 4

HCID 6420Trichloroacetyl chlorideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 55299725HCID 55299725, compound2×

Product 1

HCID 68517068HCID 68517068, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8003PentaneSolvent

Procedure

3,4-Difluoro-2-methyl-1H-pyrrole (Intermediate 8; 3.8 g) was dissolved in anhydrous diethyl ether (100 ml). Anhydrous K2CO3 (12.5 g) was added followed by trichloroacetyl chloride (10 ml). The mixture was stirred at room temperature under N2 for 2 h, poured into a cold saturated solution of NaHCO3, stirred for 10 min, and extracted with ether. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give a red brown oil. Trituration with pentane (50 ml)/DCM (2 ml), at −20° C. overnight to gave the title compound as a brown powder (1.3 g). MS (ES) MH+: 262 for C7H4Cl3F2NO; NMR (CDCl3): 2.35 (d, 3H), 9.0 (brs, 1H).

Workup

  1. stirringstirred for 10 min
  2. extractionextracted with ether
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a red brown oil

Sources & evidence

ORD record
ord-0d1b0f1c7d5b44d8b7de293c845aac1e
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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