N-bromobutanimide → HCID 59444172, compound

HRID 2060046Notes

Reaction equation

HRID 2060046 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)#[N:2].[Br:13]N1C(=O)CCC1=O>S(=O)(=O)(O)O.O>[Br:13][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][C:6]=1[CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 795874-Cyanophenylacetic acid

Product 1

HCID 59444172HCID 59444172, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-cyanophenylacetic acid (1.6 g, 9.93 mmol) in 50% aqueous sulfuric acid (10 mL) was treated with N-bromosuccinimide (1.8 g, 10.11 mmol). The mixture was stirred in the dark for 18 h then diluted with water and extracted with diethyl ether to give 2-bromo-4-cyanophenylacetic acid (2.1 g, 7.00 mmol, 70.5% yield) as a white solid containing about 25% of starting material.

Workup

  1. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-d228c44c086e4050bd6acf86092a2932
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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