4-Bromophenacyl bromide → HCID 89826358, compound

HRID 2272959Notes

Reaction equation

HRID 2272959 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]#[N:13].Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=1)=[O:17]>CN(C=O)C.ClCCl>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:16](=[O:17])[CH2:15][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]#[N:13])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 11430Potassium CarbonateHCID 138277Pyrrole-2-carbonitrile

Product 1

HCID 89826358HCID 89826358, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

5.53 g (40.0 mmol) Potassium carbonate is added to a solution of 1.70 ml (20.0 mmol) pyrrole-2-carbonitrile and 8.34 g (30.0 mmol) 2,4′-dibromoacetophenone in 40 ml DMF. The resulting suspension is stirred for 1 hour at room temperature. The reaction mixture is diluted with dichloromethane and filtered with suction. The residue is washed with dichloromethane. The filtrate is evaporated and the residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 1-[2-(4-bromo-phenyl)-2-oxo-ethyl]-1H-pyrrole-2-carbonitrile as light orange solid; HPLC/MS 2.80 (B), [M+H] 289/291.

Workup

  1. filtrationfiltered with suction
  2. washThe residue is washed with dichloromethane
  3. customThe filtrate is evaporated
  4. customthe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-a914ffa5054949d3b1bab44b8892ff90
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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