N-bromobutanimide → Methyl 5-(bromomethyl)thiophene-2-carboxylate

HRID 1972104Notes

Reaction equation

HRID 1972104 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][O:10][C:11]([C:13]1[S:14][C:15]([CH3:18])=[CH:16][CH:17]=1)=[O:12]>C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:8][CH2:18][C:15]1[S:14][C:13]([C:11]([O:10][CH3:9])=[O:12])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 580756Methyl 5-methyl-2-thiophenecarboxylate

Product 1

HCID 11424851Methyl 5-(bromomethyl)thiophene-2-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6212ChloroformSolvent

Procedure

Add freshly recrystallised NBS (323.8 g, 1.81 mol) to a solution of methyl-5-methylthiophene-2-carboxylate (258 g, 1.65 mol) in chloroform (2.6 L) at room temperature, and stir. Add benzoyl peroxide (3.99 g, 0.016 mol) and heat the reaction mixture to reflux for 7 hours. Cool the reaction mixture to ambient temperature and filter through diatomaceous earth. Wash the filter cake with chloroform (250 ml). Collect the organic layers and remove the solvent to give the title compound (388 g, 100%), which is used without further purification. ESI (m/z) 236(M+H).

Workup

  1. temperatureto reflux for 7 hours
  2. filtrationfilter through diatomaceous earth
  3. washWash the filter cake with chloroform (250 ml)
  4. customCollect the organic layers
  5. customremove the solvent

Sources & evidence

ORD record
ord-d03ffbcf1aae4812ac25c4960793156c
Source dataset
uspto-grants-2013_04
Patent number
US08431706B2

Reaction notes

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