乙酐 → 3,7-Di-t-butyldibenziodolium Trifluoromethanesulfonate

HRID 376047

反应方程式

HRID 376047 反应方程式
[I:1]([O-])(=O)=O.[K+].[C:6]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(OC(=O)C)(=O)C.[OH:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35]>CC(C)=O>[F:38][C:37]([F:40])([F:39])[S:34]([O-:36])(=[O:35])=[O:33].[C:22]([C:19]1[CH:20]=[CH:21][C:16]2[C:13]3[CH:14]=[CH:15][C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:11][C:12]=3[I+:1][C:17]=2[CH:18]=1)([CH3:25])([CH3:24])[CH3:23]

参与物

6

反应物 4

HCID 7918乙酐HCID 62406三氟甲磺酸2 次HCID 741954,4-二叔丁基联苯2 次HCID 23665710Potassium Iodate

产物 1

HCID 867492343,7-Di-t-butyldibenziodolium Trifluoromethanesulfonate收率 2%

试剂、催化剂与溶剂 1

HCID 180丙酮溶剂

反应条件

温度
0 °C

实验过程

Into a 250 ml 3-neck round bottom flask equipped with a mechanical stirrer, thermometer, and inlet was charged with agitation, 4.0 grams (18.8 mmol, 1.0 eq) of potassium iodate, 5.0 grams (18.8 mmol, 1.0 eq) of 4,4'-di-t-butylbiphenyl, and 20 mL of acetic anhydride to form a mixture which was cooled to 0° C. To the mixture was added 5.63 grams (3.32 mL, 37.5 mmol, 2.0 eq) of triflic acid dropwise at such a rate that the reaction temperature did not exceed 10° C. The temperature was kept below 10° C. during the addition by the use of a cooling bath. The reaction mixture was never homogeneous and the 4,4'-di-t-butylbiphenyl did not appear very soluble in the reaction mixture. The reaction mixture turned dark almost immediately upon addition of the triflic acid. The mixture was stirred for about 14 hours at room temperature. The reaction was quenched with approximately 60 mL of water and extracted with methylene chloride. The methylene chloride layer was washed with saturated aqueous sodium bicarbonate solution and concentrated in vacuo. The residue was a dark viscous oil. This material was soluble in ether and could be precipitated with hexanes; however, the precipitate was a brown amorphous powder. Titration with acetone gave a tan solid 0.2 gram (2% yield). Melting point=233°-234° C.

后处理

  1. customInto a 250 ml 3-neck round bottom flask equipped with a mechanical stirrer
  2. customto form a mixture which
  3. customdid not exceed 10° C
  4. additionThe temperature was kept below 10° C. during the addition by the use of a cooling bath
  5. customThe reaction was quenched with approximately 60 mL of water
  6. extractionextracted with methylene chloride
  7. washThe methylene chloride layer was washed with saturated aqueous sodium bicarbonate solution
  8. concentrationconcentrated in vacuo
  9. customcould be precipitated with hexanes

来源与证据

ORD记录
ord-aa404a0244c8481dba3e69f4e9267faa
来源数据集
uspto-grants-1996_01
专利号
US05488147

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