N-bromobutanimide → HCID 66643774, compound

HRID 1798684Notes

Reaction equation

HRID 1798684 reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][C:5]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)=[CH:4][C:3]1=[O:15].C1C(=O)N([Br:24])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:24][C:4]1[C:3](=[O:15])[C:2]([CH3:16])([CH3:1])[O:6][C:5]=1[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 595801574-(5,5-Dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile

Product 1

HCID 66643774HCID 66643774, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile (1.2 g, 5.60 mmol) in CHCl3 (12 mL), NBS (1.1 g, 6.00 mmol) was added portionwise at RT. The reaction mixture was then stirred for 3 h and diluted with DCM (100 mL). The combined organic layers were washed with water (30 mL) and brine (30 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-(3-bromo-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile (0.50 g, 31%) as an off white solid.

Workup

  1. washThe combined organic layers were washed with water (30 mL) and brine (30 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-845475c6a3f240ba83a9c385ff6d8e3b
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

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