Boron trifluoride etherate → Methyl 3-amino-6-bromo-2-nitrobenzoate

HRID 1768452Notes

Reaction equation

HRID 1768452 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([Br:10])=[CH:8][CH:7]=[C:6]([NH:11]C(=O)C)[C:5]=1[N+:15]([O-:17])=[O:16].B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>CO>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([Br:10])=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 11151255Methyl 3-acetylamino-6-bromo-2-nitrobenzoate

Product 1

HCID 58891824Methyl 3-amino-6-bromo-2-nitrobenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-acetylamino-6-bromo-2-nitro-benzoic acid methyl ester (iii, 5.53 g, 17.42 mmol) and BF3.Et2O (10.0 mL, 78.91 mmol) in MeOH (100 mL) was heated to reflux for 2 h and cooled to room temperature. The reaction mixture was neutralized with solid NaHCO3 and the solvent was removed under reduced pressure. The solid residu was dissolved in EtOAc (400 mL) and washed with H2O (3×200 mL), brine (1×200 mL), and dried with Na2SO4. The solvent was removed under reduced pressure to yield the desired product iv as an orange solid (4.74 g, 100%). 1H NMR (CDCl3): δ 7.40 (d, J=9.3 Hz, 1H), 6.70 (d, J=9.3 Hz, 1H), 6.09 (br s, 2H), 3.90 (s, 3H). Anal. Calcd for C8H7BrN2O4: C, 34.93; H, 2.57; N, 10.18. Found: C, 35.08; H, 2.49; N, 10.06.

Workup

  1. temperatureto reflux for 2 h
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe solid residu was dissolved in EtOAc (400 mL)
  4. washwashed with H2O (3×200 mL), brine (1×200 mL)
  5. dry with materialdried with Na2SO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f6c94ab4b97045c192fdbcff2632d9d1
Source dataset
uspto-grants-2007_06
Patent number
US07235662B2

Reaction notes

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