Iodine → Methyl 4-(3-iodo-4-methoxyphenyl)-3-methylbenzoate

HRID 545586Notes

Reaction equation

HRID 545586 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[CH3:19])=[CH:5][CH:4]=1.CO.C(OCC)(=O)C.[I:28]I>[Cl-].[Na+].O.S([O-])([O-])(=O)=O.[Ag+2]>[I:28][C:8]1[CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[CH3:19])[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

Participants

7

Reactant 4

HCID 807IodineHCID 887MethanolHCID 8857Ethyl AcetateHCID 67065985Methyl 4-(4-methoxyphenyl)-3-methylbenzoate

Product 1

HCID 57692978Methyl 4-(3-iodo-4-methoxyphenyl)-3-methylbenzoate

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

Methyl 4′-methoxy-2-methylbiphenyl-4-carboxylate (1.2 g, 4.68 mmol), methanol (20 mL), ethyl acetate (5 mL), iodine (1.19 g, 4.68 mmol), and silver sulfate (1.46 g, 4.68 mmol) were stirred at room temperature for 2 hours to complete the reaction. Volatiles were removed under reduced pressure to afford a yellow solid. The resulting solid was treated with brine followed by ethyl acetate extractions. The combined extracts were dried over Na2SO4 followed by filtration and concentration to afford a purple oil. The resulting oil was purified on SiO2 (Biotage HorizonFlash system, 40+M cartridge) to afford a white powder as the desired methyl 3′-iodo-4′-methoxy-2-methylbiphenyl-4-carboxylate. LCMS calc.=382.01; found=383.15 (M+1)+.

Workup

  1. customthe reaction
  2. customVolatiles were removed under reduced pressure
  3. customto afford a yellow solid
  4. extractionfollowed by ethyl acetate extractions
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfollowed by filtration and concentration
  7. customto afford a purple oil
  8. customThe resulting oil was purified on SiO2 (Biotage HorizonFlash system, 40+M cartridge)

Sources & evidence

ORD record
ord-297b3c78c5594f248ad72fa495f530c9
Source dataset
uspto-grants-2011_05
Patent number
US07935727B2

Reaction notes

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