Iodine → 3-Iodo-4-propylbenzoic acid

HRID 710407Notes

Reaction equation

HRID 710407 reaction equation
[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[I:13]I>C(Cl)Cl>[I:13][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[CH2:1][CH2:2][CH3:3])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 807IodineHCID 1376014-Propylbenzoic acid

Product 1

HCID 448288293-Iodo-4-propylbenzoic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-propylbenzoic acid (0.3 g; 1.83 mmol), CF3SO3Ag (0.47 g; 1.83 mmol) and I2 (0.46 g; 1.83 mmol) in CH2Cl2 was stirred for 48 h at room temperature, then filtered through Celite pad, washed with fresh CH2Cl2 (2×15 ml). The combined filtrates were washed with 5% NaHSO3, H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated under reduced pressure to give the title compound (0.49 g; 92%) as creamy solid. 1H-NMR (CDCl3) 1.0 (tr, 3H, J=9 Hz); 1.57-1.7 (m, 2H); 1.72-1.77 (m, 2H); 7.28 (d, 1H, 9 Hz); 7.98 (dd, 1H, J=3, 6 Hz); 8.53 (d, 1H, J=3 Hz).

Workup

  1. filtrationfiltered through Celite pad
  2. washwashed with fresh CH2Cl2 (2×15 ml)
  3. washThe combined filtrates were washed with 5% NaHSO3, H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customfiltrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-19c3e3d479dd49e6848122728e3d4eba
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

Loading…