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

HRID 1776324Notes

Reaction equation

HRID 1776324 reaction equation
[CH3:1][C:2]1([CH3:17])[C:6](=[O:7])[CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[O:3]1.C1C(=O)N([Br:25])C(=O)C1>C(Cl)(Cl)Cl>[Br:25][C:5]1[C:6](=[O:7])[C:2]([CH3:17])([CH3:1])[O:3][C:4]=1[C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 593547702,2-dimethyl-5-(4-nitrophenyl)furan-3(2H)-one

Product 1

HCID 593547574-bromo-2,2-dimethyl-5-(4-nitrophenyl)furan-3(2H)-oneYield 44%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 0° C. stirred solution of crude 2,2-dimethyl-5-(4-nitrophenyl)furan-3(2H)-one (170 mg, 0.73 mmol, 1 eq) in CHCl3 (10 mL) was added NBS (259 mg, 1.45 mmol, 2 eq), and the reaction mixture was then stirred at RT for 2 h. The chloroform was removed and the crude material was then purified via silica gel column chromatography eluting with 10% EtOAc in hexanes to afford 4-bromo-2,2-dimethyl-5-(4-nitrophenyl)furan-3(2H)-one (100 mg, 44%) as a yellow solid.

Workup

  1. customThe chloroform was removed
  2. customthe crude material was then purified via silica gel column chromatography
  3. washeluting with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-2e47b366955c4912b0265ed6653b4bc5
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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