Chlorobenzene → Bis(4-chlorophenyl)iodonium trifluoromethanesulfonate

HRID 726914

반응식

HRID 726914 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)=O.[K+].[OH:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15].[O-]S(C(F)(F)F)(=O)=O.ClC1C=CC=CC=1[I+:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1>C(OC(=O)C)(=O)C.C(Cl)Cl.O>[F:18][C:17]([F:20])([F:19])[S:14]([O-:16])(=[O:15])=[O:13].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I+:36][C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 7964ChlorobenzeneHCID 62406Trifluoromethanesulfonic acidHCID 19708102HCID 19708102, 화합물HCID 23665710Potassium Iodate

생성물 1

HCID 22389797Bis(4-chlorophenyl)iodonium trifluoromethanesulfonate수율 8.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 7918Acetic Anhydride용매

반응 조건

온도
0 °C

실험 절차

To a mixture of 20.0 grams (178 mmol, 1 eq) of chlorobenzene in 30 mL of acetic anhydride and 19.0 grams (88.8 mmol, 0.5 eq) of potassium iodate cooled to 0° C. was added 26.7 grams (15.7 mL, 178 mmol, 1.0 eq) of triflic acid at such a rate that the reaction temperature did not exceed 0° C. The mixture was allowed to warm to room temperature slowly and stirred for 14 hours. Approximately 45 mL of water was added to the reaction mixture at 0°-20° C. followed by methylene chloride. The precipitate dissolved in the methylene chloride and the organic phase was washed with water, aqueous sodium bicarbonate, and water, and concentrated in vacuo. This material was recrystallized from a mixture of 20 mL of isopropanol and 35 mL of hexane to give 7.62 grams (8.6% yield). A second crop was obtained from the mother liquor, 2.5 grams (total yield 11.4%). The product contains less than 7% of the isomeric 2-chlorophenyl-4-chlorophenyliodonium triflate and a small amount of uncharacterized impurity.

후처리

  1. customdid not exceed 0° C
  2. temperatureto warm to room temperature slowly
  3. washthe organic phase was washed with water, aqueous sodium bicarbonate, and water
  4. concentrationconcentrated in vacuo
  5. customThis material was recrystallized from a mixture of 20 mL of isopropanol and 35 mL of hexane
  6. customto give 7.62 grams (8.6% yield)
  7. customA second crop was obtained from the mother liquor, 2.5 grams (total yield 11.4%)

출처 및 근거

ORD 기록
ord-bb5b5e5a7c8b45098523c14273ff6ddc
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05710320

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