Hydrochloric Acid → (4-Benzoyl-2,6-diiodophenoxy)-acetic Acid Benzyl Ester

HRID 1839907Notes

Reaction equation

HRID 1839907 reaction equation
[OH:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][C:3]=1[I:17].Br[CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:1][C:2]1[C:3]([I:17])=[CH:4][C:5]([C:9](=[O:10])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:7]=1[I:8])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 9911585(4-Hydroxy-3,5-diiodo-phenyl)-phenyl-methanone

Product 1

HCID 9873430(4-Benzoyl-2,6-diiodophenoxy)-acetic Acid Benzyl EsterYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-hydroxy-3,5-diiodophenyl)-phenyl-methanone (as prepared in Example 6, 2.25 g, 5.0 mmol) and benzyl 2-bromoacetate (1.71 g, 7.5 mmol) in 50 mL DMF was added cesium carbonate (4.1 g, 13 mmol). The resulting suspension was stirred for 15 hours, then the reaction mixture was poured into ˜150 mL 1 M HCl. A pale oil formed, and the supernatant was removed by decantation. The oil was crystallized from hot isopropanol, yielding the title compound as colorless crystals (1.13 g, 38%). 1H NMR (400 MHz, CDCl3): δ 8.18 (s, 2H), 7.77-7.74 (m, 2H), 7.63 (tt, J=7.4, 1.2 Hz, 1H), 7.54-7.50 (m, 2 H), 7.45-7.35 (m, 5H), 5.33 (s, 2H), 4.71 (s, 2H). TLC (4:1 Hex:EtOAc), Rf 0.52. LRMS (EI+) calc'd for [C22H16I2O4+H] 598.9, found 598.8.

Workup

  1. customA pale oil formed
  2. customthe supernatant was removed by decantation
  3. customThe oil was crystallized from hot isopropanol

Sources & evidence

ORD record
ord-4526f125098a44d7b5f83e81d766ddb3
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

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