N-bromobutanimide → Methyl 4-bromo-5-methoxythiophene-2-carboxylate

HRID 1845612Notes

Reaction equation

HRID 1845612 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][O:10][C:11]1[S:15][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:12]=1>CN(C)C=O>[Br:8][C:12]1[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[S:15][C:11]=1[O:10][CH3:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 12646617Methyl 5-Methoxy-2-thiophenecarboxylate

Product 1

HCID 57826524Methyl 4-bromo-5-methoxythiophene-2-carboxylateYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NBS (903 mg, 5.07 mmol) was added in portions to a 5 mL sealed tube reactor containing methyl 5-(methyloxy)-2-thiophenecarboxylate (0.73 g, 4.23 mmol) in N,N-Dimethylformamide (DMF) (20 mL) at room temperature and the reaction stirred for 1 hour. Additional NBS (249 mg) was added and after 1 h at room temperature the product was partitioned between CHCl3 and H2O. The organic layer was dried with Na2SO4, adsorbed onto silica and purified via column chromatography (0-25% EtOAc/Hexanes) affording the title compound (825 mg, 3.19 mmol, 75%): LC-MS (ES) m/z=252 (M+H)+.

Workup

  1. customsealed tube reactor
  2. customwas partitioned between CHCl3 and H2O
  3. dry with materialThe organic layer was dried with Na2SO4
  4. custompurified via column chromatography (0-25% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-40437e0fae314a048f27125d50f8bd3e
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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