4-Chlorobenzoyl chloride → [4-Bromo-5-(4-chlorobenzoyl)-1H-pyrrol-2-yl]acetonitrile

HRID 2071694Notes

Reaction equation

HRID 2071694 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][C:8]#[N:9])[NH:5][CH:6]=1.[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][C:8]#[N:9])[NH:5][C:6]=1[C:15](=[O:16])[C:14]1[CH:18]=[CH:19][C:11]([Cl:10])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 21411906(4-Bromo-1H-pyrrol-2-yl)acetonitrile

Product 1

HCID 21411822[4-Bromo-5-(4-chlorobenzoyl)-1H-pyrrol-2-yl]acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.90 g (0.005 mole) of 4-bromopyrrole-2-acetonitrile and 0.87 g of p-chlorobenzoyl chloride (0.0005 mole) in 10 ml of methylene chloride is chilled in a dry-ice acetone bath to -30° C and is stirred while treated with 0.58 mg of anhydrous stannic chloride (0.005 mole). An orange solid precipitates. The reaction mixture is allowed to warm slowly over 1 hour to 5° C and is poured and scraped into ice-water. The whole is extracted with chloroform and the combined organic layers are washed successively with aqueous N,N-dimethylamino-1,3-propanediamine, 3N hydrochloric acid, aqueous sodium bicarbonate solution, and brine, and are dried over sodium sulfate. The viscous oil which results from evaporation of the solvent is vacuo is chromatographed on silica gel (Mallinkrodt CC-7) packed with benzene and eluated with a benzene-ether gradient. The desired material is eluted with 15% ether in benzene and recrystallized from methanol to give 4-bromo-5-(p-chlorobenzoyl)pyrrole-2-acetonitrile as a beige solid; m.p. 185°-186° C.

Workup

  1. customAn orange solid precipitates
  2. temperatureto warm slowly over 1 hour to 5° C
  3. additionis poured
  4. extractionThe whole is extracted with chloroform
  5. washthe combined organic layers are washed successively with aqueous N,N-dimethylamino-1,3-propanediamine, 3N hydrochloric acid, aqueous sodium bicarbonate solution, and brine
  6. dry with materialare dried over sodium sulfate
  7. customThe viscous oil which results from evaporation of the solvent
  8. customis chromatographed on silica gel (Mallinkrodt CC-7)
  9. washThe desired material is eluted with 15% ether in benzene
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8bb173dc09784c2a9829dda727107b95
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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