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

HRID 356795

반응식

HRID 356795 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 220160409-(2-Biphenylyl)-2,7-dicarbethoxy-9-fluorenol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

The 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 is added dropwise over a period of 2 hours to a boiling solution of 13 g (40 mmol) of 2,7-dicarbethoxy-9-fluorenone in 100 ml of dry diethyl ether. After the addition is complete, the mixture is boiled for a further 3 hours. After cooling overnight, the precipitated solid is filtered off with suction and washed with cold ether. The magnesium complex filtered off with suction is 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 is filtered off with suction, washed with water and sucked dry. For the ring-closure reaction, the dried fluorenol is boiled in 100 ml of glacial acetic acid for 6 hours, after addition of 3 drops of concentrated HCl. The mixture is allowed to crystallize overnight, the product formed is filtered off with suction and washed with glacial acetic acid and water.

후처리

  1. additionAfter the addition
  2. temperatureAfter cooling overnight
  3. filtrationthe precipitated solid is filtered off with suction
  4. washwashed with cold ether
  5. filtrationThe magnesium complex filtered off with suction
  6. waitAfter 1 hour

출처 및 근거

ORD 기록
ord-96dfef8c57c04ff1bc110cab61a9a257
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840217

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