Water → HCID 21459552, compound

HRID 1941004Notes

Reaction equation

HRID 1941004 reaction equation
[Br:1][C:2]1[NH:3][C:4]([Br:10])=[C:5]([Br:9])[C:6]=1[C:7]#[N:8].CC(C)([O-])C.[K+].Cl[C:18]([O:20][CH3:21])=[O:19].O>O1CCCC1>[Br:10][C:4]1[N:3]([C:18]([O:20][CH3:21])=[O:19])[C:2]([Br:1])=[C:6]([C:7]#[N:8])[C:5]=1[Br:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 10471741HCID 10471741, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21459552HCID 21459552, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,4,5-tribromopyrrole-3-carbonitrile (3.0 g, 0.091 mol) in tetrahydrofuran is treated portionwise with potassium t-butoxide (1.33 g, 0.012 mol) at room temperature, stirred for 20 minutes, treated dropwise with a solution of methyl chloroformate (1.29 g, 0.014 mol) in tetrahydrofuran, stirred for 21/2 days, poured into water and extracted with ether. The combined ether extracts are washed with brine, dried over MgSO4 and concentrated in vacuo to give a brown solid residue. The residue is recrystallized from ethyl acetate/hexanes to afford the title compound as a tan solid, 1.4 g (39.5%) mp 119.5° to 122.0° C.

Workup

  1. stirringstirred for 21/2 days
  2. extractionextracted with ether
  3. washThe combined ether extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a brown solid residue
  7. customThe residue is recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-01993e9b7a6f46eb9e603b9fee26db8c
Source dataset
uspto-grants-1997_12
Patent number
US05702681

Reaction notes

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