Trichloroacetyl chloride → HCID 67367650, compound

HRID 1910928Notes

Reaction equation

HRID 1910928 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[C:15]([O:17][CH2:18]C)=[O:16])=[CH:4][CH:3]=1.[Cl:21][C:22]([Cl:27])([Cl:26])[C:23](Cl)=[O:24].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][N:10]2[CH:14]=[C:13]([C:23](=[O:24])[C:22]([Cl:27])([Cl:26])[Cl:21])[CH:12]=[C:11]2[C:15]([O:17][CH3:18])=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 67366177HCID 67366177, compound

Product 1

HCID 67367650HCID 67367650, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 1-[2-(4-Chlorophenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate (150 mg, 0.54 mmol) in CH2Cl2 (10 ml) was added trichloroacetyl chloride (120 μL, 1.1 mmol) and aluminium chloride (290 mg, 2.2 mmol). After 16 h the reaction was quenched by the addition of a saturated aqueous solution of NaHCO3 (50 mL) and extracted with CH2Cl2 (3×50 mL). The organic extracts were combined, dried (MgSO4) and concentrated in vacuo to give a residue that was purified using flash chromatography (2× Biotage SP4, 12 g cartridge, 20-100% EtOAc gradient in n-hexanes) to give methyl 1-[2-(4-chlorophenyl)-2-oxoethyl]-4-(trichloroacetyl)-1H-pyrrole-2-carboxylate (97 mg, yield 42%) as a brown solid. 1H NMR (400 MHz, d6-acetone): δ 3.75 (s, 3H), 6.12 (s, 2H), 7.56 (d, 1H, J 2.0 Hz), 7.64-7.68 (m, 2H), 8.10-8.14 (m, 2H), 8.15 (d, 1H, J 2.0 Hz).

Workup

  1. customAfter 16 h the reaction was quenched by the addition of a saturated aqueous solution of NaHCO3 (50 mL)
  2. extractionextracted with CH2Cl2 (3×50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a residue that
  6. customwas purified

Sources & evidence

ORD record
ord-4515d72340574940b2bc8551d29a5499
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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