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

HRID 1508559노트

반응식

HRID 1508559 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 159865Silver sulfate촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2ae7fe74232746579f1de0d8dfaaf2ef
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221834B2

반응 노트

불러오는 중…