Hydrochloric Acid → 4-(3-Bromobenzyloxy)-3,5-diiodo-benzoic Acid 3-bromobenzyl Ester

HRID 1839902Notes

Reaction equation

HRID 1839902 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:12])[C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Br.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][O:6][C:5](=[O:7])[C:4]1[CH:3]=[C:2]([I:1])[C:10]([O:11][CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([Br:13])[CH:15]=2)=[C:9]([I:12])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 12065Ioxynic acidHCID 699793-Bromobenzyl bromide

Product 1

HCID 121488754-(3-Bromobenzyloxy)-3,5-diiodo-benzoic Acid 3-bromobenzyl EsterYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3,5-diiodo-4-hydroxybenzoic acid (0.39 g, 1.0 mmol), 3-bromobenzyl bromide (0.62 g, 2.5 mmol), and cesium carbonate (0.98 g, 3.0 mmol) in 10 mL DMF was stirred for 15 hours at room temperature. The mixture was then poured into 1 M HCl (100 mL) and a white precipitate formed. The precipitate was isolated by filtration and was recrystallized from hot isopropanol/chloroform, yielding the title compound as bright white crystals (610 mg, 84%). 1H NMR (400 MHz, CDCl3): δ 8.51 (s, 2H), 7.88 (d, J=7.6 Hz, 1H), 7.62 (d, J=8 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 7.47-7.34 (m, 3H), 7.26-7.21 (m, 2H), 5.44 (s, 2H), 5.15 (s, 2H). TLC (9:1 Hex:EtOAc), Rf 0.49.

Workup

  1. customa white precipitate formed
  2. customThe precipitate was isolated by filtration
  3. customwas recrystallized from hot isopropanol/chloroform

Sources & evidence

ORD record
ord-db06037470e74686b9e04c9ade50cc95
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

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