Methyl iodide → HCID 21459550, compound

HRID 1940999Notes

Reaction equation

HRID 1940999 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° to 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-326ad380f3cc4028bb35f2afc1d12504
Source dataset
uspto-grants-1997_12
Patent number
US05702681

Reaction notes

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