N-bromobutanimide → 4-bromo-2,2-dimethyl-5-(thiazol-4-yl)furan-3(2H)-one

HRID 1425903Notes

Reaction equation

HRID 1425903 reaction equation
[CH3:1][C:2]1([CH3:13])[C:6](=[O:7])[CH:5]=[C:4]([C:8]2[N:9]=[CH:10][S:11][CH:12]=2)[O:3]1.C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:21][C:5]1[C:6](=[O:7])[C:2]([CH3:13])([CH3:1])[O:3][C:4]=1[C:8]1[N:9]=[CH:10][S:11][CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 593548052,2-dimethyl-5-(thiazol-4-yl)furan-3(2H)-one

Product 1

HCID 593548524-bromo-2,2-dimethyl-5-(thiazol-4-yl)furan-3(2H)-oneYield 71%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,2-dimethyl-5-(thiazol-4-yl) furan-3(2H)-one (90 mg, 0.46 mmol) in CHCl3 (1.8 mL) was added NBS (0.12 g, 0.69 mmol) portionwise at RT and the reaction mixture was stirred for 1 h. The reaction mixture was diluted with DCM (10 mL), washed with water (5 mL), brine (10 mL), dried over Na2SO4, filtered and then concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 4-bromo-2,2-dimethyl-5-(thiazol-4-yl) furan-3(2H)-one (40 mg, 71%) as an off white solid.

Workup

  1. washwashed with water (5 mL), brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto obtain the crude product
  6. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-a54606957fec48c5b742222194b645df
Source dataset
uspto-grants-2015_01
Patent number
US08933074B2

Reaction notes

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