N-bromobutanimide → HCID 59849200, compound

HRID 604284Notes

Reaction equation

HRID 604284 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([O:13][CH3:14])[C:5]=1[CH3:15].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([O:13][CH3:14])[C:5]=1[CH2:15][Br:17]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 59849172HCID 59849172, compound

Product 1

HCID 59849200HCID 59849200, compoundYield 128.3%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 3-Methoxy-2-methyl-6-nitro-benzoic acid methyl ester (4.1 g, 18.2 mmol) and N-bromosuccinimide (3.89 g, 21.8 mmol) in 50 mL of CCl4 is added 2,2′-azobisisobutyronitrile (299 mg, 1.82 mmol) at room temperature. The reaction mixture is stirred at 85° C. for 21 hours and then cooled to room temperature. The reaction mixture is cooled to room temperature and then quenched by crushed ice. The mixture is extracted with ethyl acetate and washed with aqueous NaHCO3 solution followed by brine, dried over Na2SO4, filtered and evaporated in vacuo to afford the 2-Bromomethyl-3-methoxy-6-nitro-benzoic acid methyl ester (7.1 g) as orange oil. 1H-NMR (400 MHz, δ, ppm) CDCl3: 4.0 (s, 3H), 4.05 (s, 3H), 4.52 (s, 2H), 7.02 (d, 1H), 8.2 (d, 1H).

Workup

  1. temperaturecooled to room temperature
  2. temperatureThe reaction mixture is cooled to room temperature
  3. customquenched
  4. customby crushed ice
  5. extractionThe mixture is extracted with ethyl acetate
  6. washwashed with aqueous NaHCO3 solution
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-55b8aea4431d4292920a712b22a935c0
Source dataset
uspto-grants-2011_03
Patent number
US07910585B2

Reaction notes

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