Hydrochloric Acid → HCID 131724109, compound

HRID 989413Notes

Reaction equation

HRID 989413 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:14])[C:11]([OH:13])=[O:12])[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(=O)([O-])[O-].[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:12][C:11](=[O:13])[CH:10]([C:4]1[CH:3]=[C:2]([I:1])[C:7]([O:8][CH2:10][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=2)=[C:6]([I:9])[CH:5]=1)[CH3:14]

Participants

6

Reactant 4

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

Product 1

HCID 131724109HCID 131724109, compoundYield 183.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3,5-diiodo-4-hydroxyphenypropionic 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 h 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 (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).

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-08a6712defea4be6a6831309fda1e209
Source dataset
uspto-grants-2003_10
Patent number
US06638977B1

Reaction notes

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