Hydrochloric Acid → HCID 9897455, compound

HRID 1839904Notes

Reaction equation

HRID 1839904 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:14])C(O)=O)[CH:5]=[C:6]([I:9])[C:7]=1[OH:8].[I:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]Br.[C:24](=[O:27])([O-])[O-:25].[Cs+].[Cs+].Cl>CN(C=O)C>[I:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][O:25][C:24](=[O:27])[CH2:14][CH2:10][C:4]1[CH:5]=[C:6]([I:9])[C:7]([O:8][CH2:10][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=2)=[C:2]([I:1])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 27593613-Iodobenzyl bromideHCID 15128202HCID 15128202, compound

Product 1

HCID 9897455HCID 9897455, compoundYield 183.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3,5-diiodo-4-hydroxyphenylpropionic acid (209 mg, 0.5 mmol), 3-iodobenzyl bromide (371 mg, 1.25 mmol), and cesium carbonate (490 mg, 1.5 mmol) in 5 mL DMF was stirred for 15 hours at room temperature. After that time, 1 M HCl (15 mL) was added and an oil formed. The oil was extracted with ether and methanol was added. Crystals formed in the solution upon cooling, yielding the title compound as white crystals (390 mg, 92%). 1H NMR (400 MHz, CDCl3): δ 8.00 (s, 1H), 7.71-7.60 (m, 6H), 7.29-7.26 (m, 1H), 7.16 (appar. t, J=7.8 Hz, 1H), 7.11 (appar. t, J=7.8 Hz, 1H), 5.05 (s, 2H), 4.91 (s, 2H), 2.87 (t, J=7.6 Hz, 2H), 2.67 (t, J=7.6 Hz, 2H). TLC (9:1 Hex:EtOAc), Rf 0.29.

Workup

  1. customan oil formed
  2. extractionThe oil was extracted with ether and methanol
  3. additionwas added
  4. customCrystals formed in the solution
  5. temperatureupon cooling

Sources & evidence

ORD record
ord-41f2454c876f4157b67ce350fc30bedf
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

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