Stannous chloride dihydrate → Methyl 5-amino-2-bromobenzoate

HRID 2417297Notes

Reaction equation

HRID 2417297 reaction equation
O.O.[Sn](Cl)Cl.[CH3:6][O:7][C:8](=[O:19])[C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[Br:18]>CO.Cl>[CH3:6][O:7][C:8](=[O:19])[C:9]1[C:10]([Br:18])=[CH:11][CH:12]=[C:13]([NH2:15])[CH:14]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 245494Methyl 2-Bromo-5-nitrobenzoate

Product 1

HCID 245495Methyl 5-amino-2-bromobenzoate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Tin (II) chloride dihydrate (22.56 g, 100 mmol) was added to a stirred solution of methyl-2-bromo-5-nitrobenzoate (9 g, 34.61 mmol) in methanol (250 mL) and conc. HCl (25 mL). The solution was stirred at RT for 8 h and then treated with satd. aq. KHCO3 solution (600 mL). Additional solid KHCO3 (50 g) was added. The mixture was extracted with EtOAc (200 mL, 5×). The EtOAc extracts were combined, dried (MgSO4), filtered and concentrated. The residue was diluted with EtOAc (250 mL) and washed with brine (50 mL, 2×), dried (MgSO4), filtered and concentrated to obtain the title compound of this step (7.45 g, 94%) as a brown oil.

Workup

  1. additiontreated with satd
  2. extractionThe mixture was extracted with EtOAc (200 mL, 5×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe residue was diluted with EtOAc (250 mL)
  7. washwashed with brine (50 mL, 2×)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d4d02bd02969462eb0caa5318e869292
Source dataset
uspto-grants-2004_11
Patent number
US06825355B2

Reaction notes

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