2-Bromobiphenyl → 9-(2-Biphenylyl)-2,7-dibromo-9-fluorenol

HRID 635125

反応式

HRID 635125 の反応式
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Br:15][C:16]1[CH:28]=[CH:27][C:26]2[C:25]3[C:20](=[CH:21][C:22]([Br:29])=[CH:23][CH:24]=3)[C:19](=[O:30])[C:18]=2[CH:17]=1>C(OCC)C>[C:4]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:19]1([OH:30])[C:18]2[CH:17]=[C:16]([Br:15])[CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][C:22]([Br:29])=[CH:23][CH:24]=2

参加物

5

反応物 3

HCID 163292-BromobiphenylHCID 2599222,7-Dibromo-9-fluorenoneHCID 5462224Magnesium

生成物 1

HCID 220160479-(2-Biphenylyl)-2,7-dibromo-9-fluorenol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A Grignard reagent prepared from 0.72 g (30 mmol) of magnesium turnings and 5.1 ml (30 mmol) of 2-bromobiphenyl in 15 ml of diethyl ether was added dropwise to a boiling suspension of 10.0 g (29.6 mmol) of 2,7-dibromo-9-fluorenone in 100 ml of dry diethyl ether with stirring (in an ultrasound bath) over the course of 2 h. When addition is complete, the mixture is boiled for a further 3 hours. After cooling overnight, the precipitate which had formed was filtered off with suction and washed with cold ether. The magnesium complex which had been filtered off with suction was hydrolyzed in a solution of 15 g of ammonium chloride in 250 ml of iced water. After 1 h, the 9-(2-biphenylyl)-2,7-dibromo-9-fluorenol which formed was filtered off with suction, washed with water and was sucked dry. For the ring-closure reaction, the dried fluorenol was boiled for 6 hours in 100 ml of glacial acetic acid, after the additon of 3 drops of conc. HCl. The mixture was left to crystallize overnight, and the product which formed was filtered off with suction and washed with glacial acetic acid and water.

後処理

  1. additionWhen addition
  2. waitthe mixture is boiled for a further 3 hours
  3. temperatureAfter cooling overnight
  4. customthe precipitate which had formed
  5. filtrationwas filtered off with suction
  6. washwashed with cold ether
  7. filtrationThe magnesium complex which had been filtered off with suction
  8. waitAfter 1 h

出典と根拠

ORDレコード
ord-ba2eacacc3ea40b58dabd120001cb371
出典データセット
uspto-grants-2001_02
特許番号
US06187224B1

関連ノート

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