N-bromobutanimide → HCID 89534603, compound

HRID 2176033Notes

Reaction equation

HRID 2176033 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 90370165HCID 90370165, compound

Product 1

HCID 89534603HCID 89534603, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 5.27 g of benzyl 5-methylthiophene-2-carboxylate and 100 mL of carbon tetrachloride were added 4.18 g of N-bromosuccinimide (NBS) and 142 mg of azobisisobutyronitrile (AIBN), followed by stirring overnight at 80° C. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3), thereby obtaining 4.44 g of benzyl 5-(bromomethyl)thiophene-2-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-da8b347f497b44869d766cffe3a42206
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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