Iodine → 4-Bromo-4'-iodobiphenyl

HRID 336073

反応式

HRID 336073 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[I:14](O)(=O)=O.II>C(O)(=O)C.S(=O)(=O)(O)O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

参加物

7

反応物 3

HCID 807IodineHCID 71014-BromobiphenylHCID 24345Iodic acid

生成物 1

HCID 109044524-Bromo-4'-iodobiphenyl収率 325.1%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
65 °C

実験手順

A 4-neck one liter round bottom flask equipped with mechanical stirrer, thermometer and reflux condenser topped with nitrogen bubbler inlet was charged with 4-bromobiphenyl (23.31 g, 100 mmol) in acetic acid (400 mL), sulfuric acid (10 mL) and water (20 mL). To this stirring mixture was added iodic acid (4.84 g, 27.5 mmol) followed immediately by addition of iodine chips (11.17 g, 44.0 mmol). The reaction flask was immersed in a preheated tri(ethylene glycol) heating bath and heated at 65° C. internal temperature. After 30 min the bath temperature was increased such that the internal temperature raised to 85° C. after 20 min. Heating at this temperature was continued for 4.5 hours at which point HPLC analysis showed the reaction to be complete. After stirring overnight at room temperature the reaction mixture was vacuum filtered through a coarse fritted funnel and the solids were rinsed with water. The resulting white solid (32.1 g, 89% yield) had mp 177-179° C. and was used without further purification in the next step. NMR analysis confirmed the structure of Intermediate Compound 3,4-bromo-4′-iodobiphenyl. Purity (HPLC): >99%.

後処理

  1. customA 4-neck one liter round bottom flask equipped with mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. customtopped with nitrogen bubbler inlet
  4. customThe reaction flask was immersed in a preheated tri(ethylene glycol) heating bath
  5. temperatureAfter 30 min the bath temperature was increased such that the internal temperature
  6. temperatureraised to 85° C. after 20 min
  7. temperatureHeating at this temperature
  8. customthe reaction
  9. filtrationfiltered through a coarse fritted funnel
  10. washthe solids were rinsed with water

出典と根拠

ORDレコード
ord-ab2af74232b24eaaa21adf02f40882ff
出典データセット
uspto-grants-2014_11
特許番号
US08889269B2

関連ノート

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