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

HRID 1633821

反応式

HRID 1633821 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.[C:15]([C:20]1[CH:32]=[CH:31][C:30]2[C:29]3[C:24](=[CH:25][C:26]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:27][CH:28]=3)[C:23](=[O:38])[C:22]=2[CH:21]=1)([O:17][CH2:18][CH3:19])=[O:16]>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:23]1([OH:38])[C:24]2[CH:25]=[C:26]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:27]=[CH:28][C:29]=2[C:30]2[C:22]1=[CH:21][C:20]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:32][CH:31]=2

参加物

5

反応物 3

HCID 163292-BromobiphenylHCID 5462224MagnesiumHCID 149248402,7-Dicarbethoxy-9-fluorenone

生成物 1

HCID 220160409-(2-Biphenylyl)-2,7-dicarbethoxy-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 0.97 g (40 mmol) of magnesium turnings and 9.32 g (6.8 ml, 40 mmol) of 2-bromobiphenyl in 50 ml of dry diethyl ether was added dropwise to a boiling solution of 13 g (40 mmol) of 2,7-dicarbethoxy-9-fluorenone in 100 ml of dry diethyl ether in the course of 2 hours. When the addition had ended, the mixture was boiled for a further 3 hours. After cooling overnight, the precipitate which had separated out 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 ice-water. After 1 hour, the 9-(2-biphenylyl)-2,7-dicarbethoxy-9-fluorenol formed was filtered off with suction, washed with water and sucked dry. For the cyclization reaction, the dried fluorenol was boiled in 100 ml of glacial acetic acid, after addition of 3 drops of concentrated hydrochloric acid, for 6 hours. The mixture was left to crystallize overnight and the product formed was filtered off with suction and washed with glacial acetic acid and water.

後処理

  1. additionWhen the addition
  2. temperatureAfter cooling overnight
  3. customthe precipitate which had separated out
  4. filtrationwas filtered off with suction
  5. washwashed with cold ether
  6. filtrationThe magnesium complex which had been filtered off with suction
  7. waitAfter 1 hour

出典と根拠

ORDレコード
ord-0bf4fc0882e34a75afdb246bdc9616f8
出典データセット
uspto-grants-2003_01
特許番号
US06504042B1

関連ノート

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