4-Fluorobenzoyl chloride → HCID 18424154, compound

HRID 1606178Notes

Reaction equation

HRID 1606178 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:15][N:16]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>ClCCCl>[CH3:15][N:16]1[C:20]([C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)=[C:19]([CH3:21])[CH:18]=[C:17]1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 118467Ethyl 1,4-dimethyl-1H-pyrrole-2-acetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18424154HCID 18424154, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 3.95 g. (0.025 mole) of p-fluorobenzoyl chloride and 3.32 g. (0.025 mole) of aluminum chloride in 20 ml. of 1,2-dichloroethane is added dropwise to a solution of 4.52 g. (0.025 mole) of ethyl 1,4-dimethylpyrrole-2-acetate in 20 ml. of 1,2-dichloroethane at room temperature. The reaction mixture is stirred for 2 hrs. and then cooled and poured into ice-dilute HCl. The organic phase is separated and washed successively with N,N-dimethyl-1,3-propanediamine, dilute hydrochloric acid and a saturated solution of sodium chloride; dried over anhydrous magnesium sulfate; and the solvent evaporated. The residue is triturated with hot hexane and crystals form upon cooling. There is obtained about 1.9 g. (25% yield) of ethyl 1,4-dimethyl-5-(p-fluorobenzoyl)-pyrrole-2-acetate as a white solid, m.p. 84°-86°C. Upon recrystallization from methanol, the m.p. is 87°-89°C.

Workup

  1. customat room temperature
  2. temperatureand then cooled
  3. additionpoured into ice-dilute HCl
  4. customThe organic phase is separated
  5. washwashed successively with N,N-dimethyl-1,3-propanediamine, dilute hydrochloric acid
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customand the solvent evaporated
  8. customThe residue is triturated with hot hexane and crystals
  9. customform
  10. temperatureupon cooling
  11. customThere is obtained about 1.9 g

Sources & evidence

ORD record
ord-cb211e45b5c240efb18d5b87e61ff3c0
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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