Benzoyl chloride, 3-chloro- → HCID 12783775, compound

HRID 1701518Notes

Reaction equation

HRID 1701518 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:15][N:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]([O:23][CH3:24])=[O:22]>ClCCCl>[CH3:15][N:16]1[CH:20]=[C:19]([C:5](=[O:6])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[CH:18]=[C:17]1[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 69252Benzoyl chloride, 3-chloro-HCID 142178Methyl 1-methylpyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12783775HCID 12783775, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

To 100 ml 1,2-dichloroethane are added 5 g 3-chloro-benzoyl chloride followed by 8.4 g aluminium chloride. The mixture is cooled to 5° C. and 4 g methyl 1-methylpyrrole-2-carboxylate dissolved in 15 ml 1,2-dichloroethane are added thereto. The resulting mixture is stirred 0.5 hour at said temperature and then 1 hour at room temperature, after which the solution is hydrolyzed over ice, the organic phase is decanted and the solvent is evaporated off. Recrystallization of the solid residue from methanol give 7.5 g methyl 1-methyl-4-(3-chlorobenzoyl)pyrrole-2-carboxylate, m.p.=126° C.

Workup

  1. additionare added
  2. custom1 hour
  3. customat room temperature
  4. customthe organic phase is decanted
  5. customthe solvent is evaporated off
  6. customRecrystallization of the solid residue from methanol

Sources & evidence

ORD record
ord-3af27fc111fd4880a50a52e356a8685f
Source dataset
uspto-grants-1980_03
Patent number
US04194003

Reaction notes

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