Sulfuric Acid → Methyl 5-bromo-3-nitrothiophene-2-carboxylate

HRID 532422Notes

Reaction equation

HRID 532422 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]([C:10]1[S:11][CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])=[O:9].[Br:18]N1C(=O)CCC1=O.ClCCl>FC(F)(F)C(O)=O>[CH3:6][O:7][C:8]([C:10]1[S:11][C:12]([Br:18])=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])=[O:9]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 11137855Methyl 3-nitrothiophene-2-carboxylate

Product 1

HCID 57618723Methyl 5-bromo-3-nitrothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Sulfuric acid (98% strength; 12 mL) was added to a solution of 3-nitrothiophene-2-carboxylic acid methyl ester (Barker et al., Synth. Commun. 1995, 25, 3729; 20.8 g) in trifluoroacetic acid (60 mL). At 0° C., N-bromosuccinimide (21.9 g) was added in portions over a period of 45 minutes. After a further 30 minutes, the mixture was warmed to room temperature and poured into ice-water. The organic phase obtained by extraction with dichloromethane was dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel. The product with the molecular weight of 266.07 (C6H4BrNO4S) was obtained in this way; MS (ESI): 266 (M+H+).

Workup

  1. dry with materialwas dried over magnesium sulfate
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel
  4. customThe product with the molecular weight of 266.07 (C6H4BrNO4S) was obtained in this way

Sources & evidence

ORD record
ord-ee92f664e879400481565ff939d28110
Source dataset
uspto-grants-2014_10
Patent number
US08853208B2

Reaction notes

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