Toluene → Benzoic Acid

HRID 1415698Notes

Reaction equation

HRID 1415698 reaction equation
Br[C:2]1[CH:3]=[C:4](C([O-])=O)[C:5]([C:8]([O:10]C)=[O:9])=[CH:6][CH:7]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CC(C)=O.O>[C:8]([OH:10])(=[O:9])[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 86200346HCID 86200346, compound

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the mixture from Example 11 (2.07 g; 8 mmol), triethylamine (6.0 ml; 0.043 mol), and toluene (80 ml) was added diphenylphosphoryl azide (5.0 g; 0.018 mol) and the reaction mixture was heated at 80° C. for 2 hours. The reaction mixture was diluted with acetone (200 ml) and water (40 ml), heated further at 80° C. for 8 hours, cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with 15% ethyl acetate/hexane) to provide benzoic acid, 2-amino-4-bromo, methyl ester (0.514 g) as a white solid and benzoic acid, 2-amino-5-bromo, methyl ester (0.930 g) as a white solid.

Workup

  1. temperatureheated further at 80° C. for 8 hours
  2. temperaturecooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel (elution with 15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8ddee51f033940b69e5936a11a34eecb
Source dataset
uspto-grants-1999_06
Patent number
US05908840

Reaction notes

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