Hydrochloric Acid → 4-Azido-3-iodobenzoic acid

HRID 857285Notes

Reaction equation

HRID 857285 reaction equation
C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N+:11]=[N-:12])=[C:6]([I:13])[CH:5]=1.[Li+].[OH-].Cl>C1COCC1>[N:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:14])=[O:2])=[CH:5][C:6]=1[I:13])=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 15221722HCID 15221722, compound

Product 1

HCID 151795044-Azido-3-iodobenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the azido-ester from Step 2 (1.0 eq) in 6 mL of THF (0.2M) was added LiOH (2 N in H2O; 1.5 eq). The resulting mixture was stirred at 50° C. for 4 h, then acidified to pH 4 using HCl (1N) and extracted with Et2O (3×). The combined organic extracts were washed with water, brine, dried over MgSO4, filtered and concentrated to afford the 4-azido-3-iodo-benzoic acid compound as a light yellow solid.

Workup

  1. extractionextracted with Et2O (3×)
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5fe04696123d48f995aaf43df90d2e38
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

Loading…