Hydrochloric Acid → HCID 9811363, compound

HRID 1839908Notes

Reaction equation

HRID 1839908 reaction equation
[OH:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([C:9]([C:11]2[CH:16]=[C:15]([I:17])[C:14]([OH:18])=[C:13]([I:19])[CH:12]=2)=[O:10])=[CH:4][C:3]=1[I:20].Br[CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CC(N(C)C)=O>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][O:1][C:2]1[C:3]([I:20])=[CH:4][C:5]([C:9](=[O:10])[C:11]2[CH:12]=[C:13]([I:19])[C:14]([OH:18])=[C:15]([I:17])[CH:16]=2)=[CH:6][C:7]=1[I:8])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 9961859HCID 9961859, compound

Product 1

HCID 9811363HCID 9811363, compoundYield 2.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of bis-(4-hydroxy-3,5-diiodophenyl)-methanone (prepared according to Example 9, 3.59 g, 5.0 mmol) and benzyl 2-bromoacetate (1.15 g, 5.0 mmol) in 20 mL DMAc was stirred with cesium carbonate (3.3 g, 10 mmol) for 14 hours. Next was added 1 M HCl, and a yellow oil formed along with a hazy white precipitate. The precipitate was isolated by filtration and was recrystallized from hot isopropanol/chloroform, yielding the title compound as colorless crystals (98 mg, 2.2%). No attempt was made to isolate more product from the oil. 1H NMR (400 MHz, CDCl3): δ 8.11 (s, 2H), 8.10 (s, 2H), 7.45-7.35 (m, 5H), 6.22 (s, 1H), 5.33 (s, 2H), 4.72 (s, 2H). HPLC (40-90), 19.17 min. (EI−) calc'd for [C22H14I4O5—H] 864.7, found 864.6.

Workup

  1. customa yellow oil formed along with a hazy white precipitate
  2. customThe precipitate was isolated by filtration
  3. customwas recrystallized from hot isopropanol/chloroform

Sources & evidence

ORD record
ord-5a1df0c0432c4af4a2a55b9e77251d36
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

Loading…