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Water → 4-(3-Hydroxypropylsulfanyl)phenylbenzonitrile

HRID 1713305
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HRID 1713305 반응식
Br[C:2]1[CH:3]=[C:4]([S:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)#[N:14].C(=O)([O-])[O-].[Na+].[Na+].O>C(#N)C.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>[OH:12][CH2:11][CH2:10][CH2:9][S:8][C:4]1[CH:5]=[CH:6][C:7]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:13]#[N:14])=[CH:2][CH:3]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 585220973-(3-Bromophenylsulfanyl)propane-1-ol

생성물 1

HCID 674548124-(3-Hydroxypropylsulfanyl)phenylbenzonitrile수율 71.2%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

3-(3-Bromophenylsulfanyl)propane-1-ol (0.49 g) was suspended in acetonitrile (8.5 mL), 4-cyanophenylboronic acid (0.34 g), sodium carbonate (0.42 g), water (1.7 mL) and tetrakis(triphenylphosphine)palladium(0) (0.12 g) were added, and the resulting mixture was stirred at 80° C. for 7 hours. The reaction mixture was cooled to room temperature and then partitioned between ethyl acetate (35 mL) and water (10 mL). The organic layer was washed successively with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1) to give the title compound (0.38 g).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate (35 mL) and water (10 mL)
  3. washThe organic layer was washed successively with water (10 mL) and brine (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-ad5c31d107e24ae6804bfbd2b1c92f9e
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795236B2

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