Iodine → 2,5-Dichloro-3-iodobenzoic acid

HRID 274837

反応式

HRID 274837 の反応式
[I:1]I.N(OC(C)(C)C)=O.N[C:11]1[C:12]([Cl:21])=[C:13]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[C:14]([OH:16])=[O:15].N(OCCCC)=O>CS(C)=O.O>[Cl:21][C:12]1[C:11]([I:1])=[CH:19][C:18]([Cl:20])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]

参加物

7

反応物 4

HCID 807Iodine2 回HCID 8630ChlorambenHCID 10906Tert-Butyl nitriteHCID 10996Butyl nitrite

生成物 1

HCID 214781212,5-Dichloro-3-iodobenzoic acid収率 84.8%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 962Water溶媒

反応条件

温度
35 °C

実験手順

In a flask 48.35 grams (0.191 mole) of iodine was dissolved in 90 mL of dimethyl sulfoxide. To this solution was added 29.47 grams (0.286 mole) of tertiary butyl nitrite. A solution of 39.25 grams (0.191 mole) of 3-amino-2,5-dichlorobenzoic acid in 130 mL of dimethyl sulfoxide was added dropwise to the solution of iodine and butyl nitrite. During this addition the temperature rose from 20° C. to 50° C., at which temperature the addition was stopped until the reaction mixture had cooled to 35° C. The addition was then completed. When the addition was complete, the reaction mixture was stirred for approximately 16 hours, then poured into water, and this mixture was extracted with ethyl acetate. The extracts were combined and washed with an aqueous solution of sodium hydrogen sulfate and finally with water. The combined extracts were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated from the filtrate under reduced pressure, yielding 51.34 grams of 2,5-dichloro-3-iodobenzoic acid as a solid.

後処理

  1. additionDuring this addition the temperature
  2. customrose from 20° C. to 50° C., at which temperature
  3. additionthe addition
  4. additionThe addition
  5. additionWhen the addition
  6. extractionthis mixture was extracted with ethyl acetate
  7. washwashed with an aqueous solution of sodium hydrogen sulfate and finally with water
  8. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe solvent was evaporated from the filtrate under reduced pressure

出典と根拠

ORDレコード
ord-001cbe39c22a432dafc83796b36bb5c4
出典データセット
uspto-grants-1995_02
特許番号
US05391541

関連ノート

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