Water → 4-Iodo-2-phenylbenzoic acid methyl ester

HRID 2121185Notes

Reaction equation

HRID 2121185 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7](N)=[CH:6][C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N([O-])=O.[Na+].O.[I-:23].[K+]>Cl.CC(C)=O.CCOCC>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([I:23])=[CH:6][C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 962Water2×HCID 4875Potassium IodideHCID 154069885-Amino-biphenyl-2-carboxylic acid methyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 536899794-Iodo-2-phenylbenzoic acid methyl esterYield 59%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

To a 0° C. suspension of the 2-phenyl-4-aminobenzoic acid methyl ester prepared in Example 210B (4.54 g, 20 mmol) in 6.0 N HCl (20 mL) and acetone (10 mL) was added dropwise a solution of sodium nitrite (1.66 g, 24 mmol) in a minimum amount of water. After 30 minutes, potassium iodide (6.64 g, 40 mmol) in a minimum amount of water was added dropwise to the reaction mixture. The internal temperature of the reaction mixture was maintained under 5° C. for both additions. The reaction mixture was then stirred at ambient temperature for one hour. The reaction mixture was diluted with ether (200 mL), washed with water, sodium bisulfite (10% aqueous solution), water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography (8% ethyl acetate-hexane) to give 4-iodo-2-phenylbenzoic acid methyl ester (3.98 g, 59%). 1H NMR (300 MHz, CDCl3) δ 7.77 (m, 2H), 7.55 (d, 1H), 7.38 (m, 3H), 7.27 (m, 2H), 3.63 (s, 3H). Ms (CI+): 356 (M+NH4)+.

Workup

  1. washwashed with water, sodium bisulfite (10% aqueous solution), water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (8% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-aa1a15c3be7846d8b93e7a68679b6af8
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

Loading…