N-bromobutanimide → HCID 13884688, compound

HRID 979690Notes

Reaction equation

HRID 979690 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)[CH3:2].[Br:17]N1C(=O)CCC1=O.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)(Cl)Cl.C(OCC)(=O)C.CCCCCC>[Br:17][C:5]1[CH:6]=[C:7]([CH:10]([CH:14]([CH3:15])[CH3:16])[C:11]([OH:13])=[O:12])[CH:8]=[CH:9][C:4]=1[O:3][CH2:1][CH3:2]

Participants

7

Reactant 3

HCID 67184N-bromobutanimideHCID 6451240Aluminum(III) ChlorideHCID 13650218HCID 13650218, compound

Product 1

HCID 13884688HCID 13884688, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a solution of 0.15 g (0.67 mM) of 2-(4-ethoxyphenyl)isovaleric acid in 3 ml of chloroform, 0.24 g (1.35 mM) of N-bromosuccinimide was added, and the mixture was heated for 3 hours in the presence of a catalytic amount of anhydrous aluminum chloride under a reflux condition. The oily substance obtained by condensing the reaction mixture was subjected to silica gel column chromatography while using a 1:3 mixture of ethyl acetate and n-hexane as an eluent, thereby 0.12 g of 2-(3-bromo-4-ethoxyphenyl)isovaleric acid was obtained as a colourless and oily substance (yield: 60%).

Workup

  1. customThe oily substance obtained by condensing the reaction mixture

Sources & evidence

ORD record
ord-2f3d05b00229432785d3b96a8104ff15
Source dataset
uspto-grants-1987_05
Patent number
US04668815

Reaction notes

Loading…