Hydrochloric Acid → HCID 9811483, compound

HRID 1839912Notes

Reaction equation

HRID 1839912 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[C:13]([I:14])=[CH:12][C:11]([C:15](=[O:27])[C:16]([C:18]2[CH:23]=[C:22]([I:24])[C:21]([OH:25])=[C:20]([I:26])[CH:19]=2)=[O:17])=[CH:10][C:9]=1[I:28].Br[CH2:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32].Cl>CN(C=O)C.C(Cl)(Cl)Cl>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][O:7][C:8]1[C:9]([I:28])=[CH:10][C:11]([C:15](=[O:27])[C:16]([C:18]2[CH:19]=[C:20]([I:26])[C:21]([OH:25])=[C:22]([I:24])[CH:23]=2)=[O:17])=[CH:12][C:13]=1[I:14])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 9875313HCID 9875313, compound

Product 1

HCID 9811483HCID 9811483, compoundYield 14.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (1.30 g, 4.0 mmol) was suspended in a solution of 1,2-bis-(4-hydroxy-3,5-diiodophenyl)-ethane-1,2-dione (as prepared in Example 15, 1.49 g, 2.0 mmol) and benzyl 2-bromoacetate (0.46 g, 2.0 mmol) in 8 mL DMF. The mixture was stirred at RT for 16 hours and was poured into 1 M HCl. The resulting precipitate was isolated by filtration, then was dissolved in hot chloroform and filtered through Celite. The solvent was removed by rotary evaporation, and the crude material was purified by silica gel column chromatography (5% MeOH in CH2Cl2), yielding the title compound as a yellow powder (258 mg, 14%). 1H NMR (400 MHz, DMSO-d6): δ 8.30 (s, 2H), 8.23 (s, 2H), 7.45-7.34 (m, 5H), 5.27 (s, 2H), 4.73 (s, 2H). HPLC (50-90), 15.74 min. LRMS (EI−) calc'd for [C23H14I4O6—H] 893.0, found 892.6.

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. filtrationfiltered through Celite
  3. customThe solvent was removed by rotary evaporation
  4. customthe crude material was purified by silica gel column chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a6875bddfcac407e95ec8901c6dc316d
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

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