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

HRID 1508559Notes

Reaction equation

HRID 1508559 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[CH3:19])=[CH:5][CH:4]=1.[I:20]I.CO>[O-]S([O-])(=O)=O.[Ag+].[Ag+].C(OCC)(=O)C>[I:20][C:8]1[CH:7]=[C:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[CH3:19])[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 159865Silver sulfateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Into a 10000-mL 4-necked round-bottom flask was placed methyl 4-(4-methoxyphenyl)-3-methylbenzoate (470 g, 1.83 mol, 1.00 equiv), Ag2SO4 (572.8 g, 1.84 mol, 1.00 equiv), iodine (466.3 g, 1.84 mol, 1.00 equiv), methanol (4000 mL), ethyl acetate (1000 mL). The resulting solution was stirred for 3 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was diluted with 3000/1500 mL of EtOAc/brine. The solid was filtered out. The filtrate was extracted with 2×1000 mL of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 630 g (crude) of methyl 4-(3-iodo-4-methoxyphenyl)-3-methylbenzoate as a yellow solid.

Workup

  1. customInto a 10000-mL 4-necked round-bottom flask was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additionThe residue was diluted with 3000/1500 mL of EtOAc/brine
  4. filtrationThe solid was filtered out
  5. extractionThe filtrate was extracted with 2×1000 mL of ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 630 g (crude) of methyl 4-(3-iodo-4-methoxyphenyl)-3-methylbenzoate as a yellow solid

Sources & evidence

ORD record
ord-2ae7fe74232746579f1de0d8dfaaf2ef
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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