Chlorobenzene → Bis(4-chlorophenyl)iodonium trifluoromethanesulfonate

HRID 726914

反応式

HRID 726914 の反応式
[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

参加物

8

反応物 4

HCID 7964ChlorobenzeneHCID 62406Trifluoromethanesulfonic acidHCID 19708102HCID 19708102、化合物HCID 23665710Potassium Iodate

生成物 1

HCID 22389797Bis(4-chlorophenyl)iodonium trifluoromethanesulfonate収率 8.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回HCID 7918Acetic Anhydride溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-bb5b5e5a7c8b45098523c14273ff6ddc
出典データセット
uspto-grants-1998_01
特許番号
US05710320

関連ノート

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