Methyl iodide → HCID 21459550, compound

HRID 1590573Notes

Reaction equation

HRID 1590573 reaction equation
[Br:1][C:2]1[NH:3][C:4]([Br:13])=[C:5]([C:9]([F:12])([F:11])[F:10])[C:6]=1[C:7]#[N:8].[CH3:14]C(C)([O-])C.[K+].CI>O1CCCC1.O.CCOCC>[Br:1][C:2]1[N:3]([CH3:14])[C:4]([Br:13])=[C:5]([C:9]([F:10])([F:11])[F:12])[C:6]=1[C:7]#[N:8]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 21459540HCID 21459540, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21459550HCID 21459550, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2,5-dibromo-4-(trifluoromethyl)pyrrole-3-carbonitrile (0.10 g, 0.30 mmol) in tetrahydrofuran is treated with solid potassium t-butoxide (0.053 g, 0.49 mmol), stirred for 1 hour at 25° C., treated dropwise with methyl iodide (0.067 g, 0.47 mmol), stirred for 2 hours at 25° C. and for 1 hour at 50° C. and diluted with water and ether. The phases are separated and the organic phase is washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to afford the title compound as a white solid, 0.09 g, mp 101°-104° C.

Workup

  1. stirringstirred for 2 hours at 25° C. and for 1 hour at 50° C.
  2. customThe phases are separated
  3. washthe organic phase is washed sequentially with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1245159ad6d949979eb671e3b1885160
Source dataset
uspto-grants-1993_04
Patent number
US05204332

Reaction notes

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