Iodine → HCID 57704787, compound

HRID 2093136Notes

Reaction equation

HRID 2093136 reaction equation
[I:1]I.[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.CO.CCOC(C)=O>CO.S([O-])([O-])(=O)=O.[Ag+2]>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([I:1])[CH:15]=1

Participants

6

Reactant 3

HCID 807IodineHCID 21584119Ethylacetate methanolHCID 67065969HCID 67065969, compound

Product 1

HCID 57704787HCID 57704787, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixture of silver sulfate (0.97 g, 3.11 mmol) and iodine (0.79 g, 3.11 mmol) in MeOH (20 ml) at room temperature, a solution of methyl 2-chloro-4′-methoxybiphenyl-4-carboxylate (0.86 g, 3.11 mmol) in 1:1 mixture of MeOH/EtOAc (10 ml) was added. The mixture was stirred at room temperature for 6 h until color of the reaction turned to pale. The solid was filtered off and the filtrate was concentrated. The title compound was obtained after flash column using EtOAc:hexane/5:95 as the eluant. 1H NMR (CDCl3, 500 MHz): δ 8.15 (d, J=1.5 Hz, 1H), 7.97 (dd, J=8, 2Hz, 1H), 7.89 (d, J=2 Hz, 1H), 7.46 (dd, J=8.5, 2 Hz, 1H), 7.40 (d, J=8 Hz, 1H), 6.91 (d, J=8 Hz, 1H), 3.98 (s, 6H).

Workup

  1. additionwas added
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-43d71bc3598548949b972e2b55647660
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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