Isobutyronitrile → 2-Methyl-2-(diphenylbismuthanyl)-propionitrile

HRID 2261508

Reaction equation

HRID 2261508 reaction equation
[C:1](#[N:5])[CH:2]([CH3:4])[CH3:3].C(NC(C)C)(C)C.[Li].[C:14]1([Bi:20](Br)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH3:3][C:2]([Bi:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:4])[C:1]#[N:5]

Participants

5

Reactant 3

HCID 6559IsobutyronitrileHCID 13026286Diphenylbismuthanyl BromideHCID 45051747Lithium diisopropylamine

Product 1

HCID 866164602-Methyl-2-(diphenylbismuthanyl)-propionitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A 0.45 ml (5 mmole) of isobutyronitrile (Tokyo Kasei Co., Ltd.) was dissolved in 5 ml of THF, and the mixture was chilled to −78° C. under nitrogen atmosphere. Thereto was slowly added dropwise lithium diisopropylamine obtained above. The reaction mixture was stirred at −78° C. for 10 minutes and then heated to 0° C. Thereto was added dropwise a solution of 2.223 g (5 mmole) of diphenylbismuthanyl bromide prepared in Preparation Example 3 in 5 ml of THF.

Workup

  1. customobtained above
  2. temperatureheated to 0° C

Sources & evidence

ORD record
ord-ab5e418cd6464254a3f947294199fe83
Source dataset
uspto-grants-2010_12
Patent number
US07847043B2

Linked notes

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