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

HRID 2416292

반응식

HRID 2416292 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

 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.

후처리

  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

출처 및 근거

ORD 기록
ord-c0148f65d60245d8a8337a4161dcaf5c
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06822094B2

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