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

HRID 1776386
Notes
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Reaction equation

HRID 1776386 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-ea2a5685c69e49e4a4b922c2f2d2fa0d
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09265767B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes