Methyl 3-bromo-5-nitrobenzoate → Methyl 3-amino-5-bromobenzoate

HRID 1442802

Reaction equation

HRID 1442802 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[BH4-].[Na+]>CO>[NH2:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([Br:1])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 239341Methyl 3-bromo-5-nitrobenzoateHCID 4311764Sodium borohydride

Product 1

HCID 18763420Methyl 3-amino-5-bromobenzoateYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-bromo-5-nitrobenzoate (1.0 g, 3.8 mmol) in methanol (30 mL) was added NiCl2-6 H2O (1.8 g, 7.6 mmol) and NaBH4 (430 mg, 11 mmol) successively at 0° C. The reaction mixture was stirred for 30 seconds and was then quenched by the addition of water. The mixture was extracted with ethyl acetate (30 mL×3). The combined organic layers were washed with brine and water, dried over anhydrous Na2SO4, and concentrated under vacuum to afford methyl 3-amino-5-bromobenzoate (860 mg, 97% yield). 1H NMR (400 MHz, d-DMSO) δ 7.14 (dd, J=2.0, 2.4 Hz, 1H), 7.11 (t, J=2.4 Hz, 1H), 6.94 (t, J=2.8 Hz, 1H), 5.72 (brs, 2H), 3.79 (s, 3H).

Workup

  1. customwas then quenched by the addition of water
  2. extractionThe mixture was extracted with ethyl acetate (30 mL×3)
  3. washThe combined organic layers were washed with brine and water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a17d43c2aff8434d8d8c71eaea159052
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Linked notes

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