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Hydrochloric Acid → Fluorene

HRID 2352750
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HRID 2352750 반응식
C[C:2]1(C)[C:14]2[CH:13]=[C:12](B(O)O)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][C:5](B(O)O)=[CH:6][CH:7]=2.IC1C=CC2C3C(=CC(I)=CC=3)C(C)(C)C=2C=1.C([O-])([O-])=O.[Na+].[Na+].Cl>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCCCCC.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:4]1[C:3]2[CH2:2][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1
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참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 129942022,7-Diiodo-9,9-dimethyl-9H-fluorene2회HCID 24820467(9,9-Dimethyl-9H-fluorene-2,7-diyl)diboronic acid2회

생성물 1

HCID 6853Fluorene

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 1140Toluene용매
HCID 8028Tetrahydrofuran용매2회
HCID 21226206Ethyl acetate hexane용매

실험 절차

With 9,9-dimethylfluorene-2,7-diboronic acid and 2,7-diiodo-9,9-dimethyl fluorene, which are synthesized according to synthesis example 1, a Suzuki reaction is carried out. Under a nitrogen atmosphere, tetrakis(triphenylphosphine)palladium(0) (1.0 mmol) is dissolved in THF (50 ml), followed by adding thereto 2,7-diiodo-9,9-dimethyl fluorene (50 mmol), a solution of 2M Na2CO3 (50 ml) and 9,9-dimethylfluorene-2,7-diboronic acid (25 mmol)/THF (100 ml) in this order. Thereafter, after refluxing for 7 hr, a reaction is brought to an end. The solution is cooled to room temperature, followed by substituting with toluene and adding substantially 30 ml of 1N HCl, further followed by washing a toluene phase with water until neutrality is obtained. After drying with sodium sulfate, followed by filtering and distilling the solvent away, and thereby a crude product is obtained. After washing with substantially 100 ml of methanol, a colorless crystal is obtained. Furthermore, by passing through a short column from hexane/ethyl acetate to remove original components, finally followed by recrystallizing, and thereby fluorene trimer (20 mmol) is obtained.

후처리

  1. customaccording to synthesis example 1
  2. customa Suzuki reaction
  3. additionby adding
  4. temperatureThereafter, after refluxing for 7 hr
  5. washby washing a toluene phase with water until neutrality
  6. customis obtained
  7. dry with materialAfter drying with sodium sulfate
  8. filtrationby filtering
  9. distillationdistilling the solvent away
  10. customa crude product is obtained
  11. washAfter washing with substantially 100 ml of methanol
  12. customa colorless crystal is obtained
  13. customto remove original components
  14. customby recrystallizing

출처 및 근거

ORD 기록
ord-c9fe9cd5547948c48f27a6922e597452
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07749618B2

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