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

HRID 2416292

反応式

HRID 2416292 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 over a period of 2 hours. After addition was complete, the mixture was boiled for a further 3 hours. After cooling overnight, the precipitate 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 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 ring closure reaction, the dried fluorenol was boiled in 100 ml of glacial acetic acid, after addition of 3 drops of concentrated HCl, for 6 hours. The mixture was allowed to crystallize overnight, the product formed was filtered off with suction and was washed with glacial acetic acid and water.

後処理

  1. additionAfter addition
  2. temperatureAfter cooling overnight
  3. customthe precipitate formed
  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-c0148f65d60245d8a8337a4161dcaf5c
出典データセット
uspto-grants-2004_11
特許番号
US06822094B2

関連ノート

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