Ethyl bromoacetate → HCID 21459516, compound

HRID 1940994Notes

Reaction equation

HRID 1940994 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[NH:9][C:10]([Br:16])=[C:11]([Br:15])[C:12]=1[C:13]#[N:14].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>O1CCCC1>[Br:7][C:8]1[N:9]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:10]([Br:16])=[C:11]([Br:15])[C:12]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10471741HCID 10471741, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21459516HCID 21459516, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (0.75 g, 6.7 mmol) is added in portions at room temperature to a solution of 2,4,5-tribromopyrrole-3-carbonitrile (2.0 g, 6.1 mmol) in anhydrous tetrahydrofuran (20 mL). After 30 minutes, ethyl bromoacetate (1.12 g, 6.7 mmol) is added dropwise and the mixture stirred for 4-5 hours at room temperature. Work-up as described in Example 15 gives the product as white solid (0.42 g) mp 140°-143° C.

Sources & evidence

ORD record
ord-e0ceb7d6b56049488b2976d365851c3d
Source dataset
uspto-grants-1997_12
Patent number
US05702681

Reaction notes

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