Benzyl Bromide → HCID 21459530, compound

HRID 1590566Notes

Reaction equation

HRID 1590566 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+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:17]([N:3]1[C:4]([Br:10])=[C:5]([Br:9])[C:6]([C:7]#[N:8])=[C:2]1[Br:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10471741HCID 10471741, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21459530HCID 21459530, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 1.00 g (3.04 mmol) of 2,4,5-tribromopyrrole-3-carbonitrile and 0.68 g (6.1 mmol) of potassium t-butoxide in 30 mL of dry THF under a nitrogen atmosphere is added 1.10 mL of benzyl bromide. The mixture is heated to reflux and stirred overnight. After dilution with 100 mL of water and 150 mL of ethyl acetate, the organic mixture is separated and washed with salt solution, dried over magnesium sulfate, and concentrated in vacuo to leave 2.34 g of orange oil. The oil is triturated under a mixture of 5:1 hexane/ether to give a white solid collected by filtration; 0.81 g, mp 100°-103° C. The filtrate yields a second crop; 0.11 g, mp 100°-103° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. customAfter dilution with 100 mL of water and 150 mL of ethyl acetate, the organic mixture is separated
  4. washwashed with salt solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-807bc331b39d42d7ab1bfc6c49ef56d7
Source dataset
uspto-grants-1993_04
Patent number
US05204332

Reaction notes

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