Methanol → Methyl 2-amino-3-bromobenzoate

HRID 1919666Notes

Reaction equation

HRID 1919666 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2702592-Amino-3-bromobenzoic acid

Product 1

HCID 11615550Methyl 2-amino-3-bromobenzoate

Procedure

2-amino-3-bromobenzoic acid (1.00 g) was mixed with methanol (10 ml) and concentrated sulfuric acid (1 ml). The mixture was stirred at reflux for 31 hours. The solvent were evaporated, and saturated aqueous sodium bicarbonate was carefully added. The solid was extracted with CH2Cl2 (3×). The combined extracts were dried over Na2SO4 and the solvents removed in vacuo to afford methyl 2-amino-3-bromobenzoate as a semi-crystalline solid (976 mg, 91% yield). LCMS (ES): >85% pure, m/z 230 [M+1]+.

Workup

  1. temperatureat reflux for 31 hours
  2. customThe solvent were evaporated
  3. additionsaturated aqueous sodium bicarbonate was carefully added
  4. extractionThe solid was extracted with CH2Cl2 (3×)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-266a6e56c7d947bfadce34dc1283a297
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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