Ethyl Acetate → HCID 15717404, compound

HRID 2414777Notes

Reaction equation

HRID 2414777 reaction equation
Br[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Li]CCCC.[CH3:19][Se:20][Se]C.C(OCC)(=O)C>C1COCC1>[CH3:19][Se:20][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 23496DimethyldiselenideHCID 684522-Bromo-3-nitrobenzoic acidHCID 178418339Butyllithium

Product 1

HCID 15717404HCID 15717404, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 500 mg (2.0 mmol) of 2-bromo-3-nitrobenzoic acid in anhydrous THF (15 mL) was added 2.80 mL (4.47 mmol) of n-BuLi (1.6 M soln. in Hex.) slowly at −78° C. After 10 minutes, a solution of 383 mg (2.03 mmol) of dimethyl diselenide in THF (5 mL) was added. After 30 minutes, the reaction mixture was warmed to room temperature. After additional stirring for 2 hours, ethyl acetate was added. The organic layer was washed with 1 N HCl solution, dried over MgSO4, and concentrated under reduced pressure. 470 mg of crude product was obtained and used for the next reaction without further purification.

Workup

  1. waitAfter 30 minutes
  2. washThe organic layer was washed with 1 N HCl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b026afd0448946b8bd3d04a092fda704
Source dataset
uspto-grants-2004_11
Patent number
US06815459B2

Reaction notes

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