Triethylamine → Methyl 2-amino-5-bromobenzoate

HRID 2242756Notes

Reaction equation

HRID 2242756 reaction equation
[CH3:1][O:2]S([O-])(=O)=O.[NH2:7][C:8]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:9]=1[C:10](O)=[O:11].CCN(CC)CC>CN(C=O)C>[NH2:7][C:8]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:9]=1[C:10]([O:2][CH3:1])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 798582-Amino-5-bromobenzoic acidHCID 4694097Methyl sulfate(1-)

Product 1

HCID 736224Methyl 2-amino-5-bromobenzoateYield 56.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

MeSO4 (26.3 mL, 0.280 mol) was added to a solution of 2-amino-5-bromobenzoic acid (50.0 g, 0.230 mol) in DMF and Et3N (40 mL, 0.28 mol). The reaction mixture was stirred at rt for 48 h. The mixture was quenched with water, extracted with EtOAc and dried over MgSO4. The solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel (5% EtOAc in petroleum ether) to afford methyl 2-amino-5-bromobenzoate (30 g, 56% yield). 1H NMR (300 MHz, DMSO) δ 7.74 (d, J=2.7, 1H), 7.35 (dd, J=9.0, 2.1, 1H), 6.78-6.73 (m, 3H), 3.77 (s, 3H).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by chromatography on silica gel (5% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-d057828af2914d8ab8b8f5f552438d70
Source dataset
uspto-grants-2010_03
Patent number
US07671221B2

Reaction notes

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