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

HRID 1508559ノート

反応式

HRID 1508559 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 159865Silver sulfate触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2ae7fe74232746579f1de0d8dfaaf2ef
出典データセット
uspto-grants-2015_12
特許番号
US09221834B2

反応ノート

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