Water → 1-(3-Chloro-2-hydroxy-4-((4-iodobenzyl)oxy)phenyl)ethanone

HRID 1161116Notes

Reaction equation

HRID 1161116 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][CH:4]=1.[Cl:10][C:11]1[C:12]([OH:21])=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1[OH:17].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Cl:10][C:11]1[C:12]([OH:21])=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1[O:17][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 9542584-Iodobenzyl bromideHCID 574382941-(3-Chloro-2,4-dihydroxy-phenyl)ethanone

Product 1

HCID 574383881-(3-Chloro-2-hydroxy-4-((4-iodobenzyl)oxy)phenyl)ethanoneYield 29.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 1-bromomethyl-4-iodo-benzene (10.00 g, 33.7 mmol) to a solution of 1-(3-chloro-2,4-dihydroxy-phenyl)-ethanone (7.92 g, 42.4 mmol) and cesium carbonate (16.6 g, 50.9 mmol) in dimethylformamide (250 mL) and stir. After 18 hours, pour reaction into water and extract with ethyl acetate. Combine organic layers and wash with 2N NaOH. Dry with sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography eluting with a gradient of ethyl acetate:hexanes to yield the title product as a tan solid (4.00 g, 23%): 1H NMR (DMSO-d6) δ 2.62 (s, 3H), 5.33 (s, 2H), 6.87 (d, 1H), 7.27 (d, 2H), 7.78 (d, 2H), 7.94 (d, 1H), 13.13 (s, 1H).

Workup

  1. additionpour
  2. extractionextract with ethyl acetate
  3. washCombine organic layers and wash with 2N NaOH
  4. dry with materialDry with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give a residue
  8. customPurify the residue by flash chromatography
  9. washeluting with a gradient of ethyl acetate

Sources & evidence

ORD record
ord-cfc88861acda42f08105c6721c8c76f5
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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