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Borane → 3-Bromo-5-chlorophenol

HRID 1396057
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HRID 1396057 반응식
CP(C)CCP(C)C.[Br:9][C:10]1[CH:11]=[C:12]([Cl:16])[CH:13]=[CH:14][CH:15]=1.[B]1OC(C)(C)C(C)(C)[O:18]1.B.OOS([O-])=O.[K+]>CC(C)=O.O.C1CC=CCCC=C1.C1C=C[C]2[CH][CH][CH][C]2C=1.[Ir]>[Br:9][C:10]1[CH:15]=[C:14]([OH:18])[CH:13]=[C:12]([Cl:16])[CH:11]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 6331BoraneHCID 79281-Bromo-3-chlorobenzeneHCID 1410591,2-Bis(dimethylphosphino)ethaneHCID 6364989PinacolboraneHCID 23707502Potassium hydroxy sulfite

생성물 1

HCID 226301803-Bromo-5-chlorophenol수율 62%

시약·촉매·용매 3

HCID 178420247
(1,5-cyclooctadiene)-eta5-indenyl)iridium(I)
촉매
HCID 180Acetone용매
HCID 962Water용매

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온도
150 °C

실험 절차

Under an atmosphere of dry nitrogen, 103 mg 1,5-cyclooctadiene(H5-indenyl)iridium (I) was put in a 25 mL Pyrex bottle. Subsequently were added 0.04 mL 1,2-bis(dimethylphosphino)ethane, 0.61 mL 3-bromochlorobenzene and 1.52 mL pinacolborane. The mixture was stirred at 150° C. for 3.5 h. After cooling to room temperature, the borane adduct was taken up in 17 mL acetone to give a clear solution. This solution was added slowly to 17.41 mL of a 0.30 M solution of oxone in water cooled in an ice bath. The mixture was stirred vigorously for 15 min. at room temperature and extracted three times with DCM. The combined organic phases were dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (DCM) to yield 750 mg (62%) of a beige solid. 1H NMR complies with known data (compound (1), Maleczka, 2003).

후처리

  1. temperatureAfter cooling to room temperature
  2. customto give a clear solution
  3. temperaturecooled in an ice bath
  4. stirringThe mixture was stirred vigorously for 15 min. at room temperature
  5. extractionextracted three times with DCM
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography (DCM)

출처 및 근거

ORD 기록
ord-97150a3b1f58414499f4b9460bae2055
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901108B2

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