Ethyl Acetate → HCID 178498468, compound

HRID 1966266Notes

Reaction equation

HRID 1966266 reaction equation
C[O:2][C:3]1[C:8]([C:9]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=[CH:5][N:4]=1.B(Br)(Br)Br.C(OCC)(=O)C>ClCCl>[OH:2][C:3]1[C:8]([C:9]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 58027029HCID 58027029, compound

Product 1

HCID 178498468HCID 178498468, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-(2-methoxypyridin-3-yl)-5-nitrobenzoate (Reference Compound No. 1-3-(1), 200 mg, 0.694 mmol) was dissolved in anhydrous dichloromethane (2 mL), then boron tribromide (118 μL, 1.25 mmol) was added thereto at −78° C. The reaction mixture was stirred at 0° C. for 3 hours, and then poured into ice-water (30 mL). Ethyl acetate (50 mL) was added, and then separated. The organic layer was washed with saturated brine (50 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (102 mg) as a yellow solid. (Yield 54%)

Workup

  1. customat −78° C
  2. customseparated
  3. washThe organic layer was washed with saturated brine (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2b8262cb0c414cb08f8238967d3b0840
Source dataset
uspto-grants-2013_04
Patent number
US08420635B2

Reaction notes

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