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Water → 4-(3-Hydroxypropylsulfanyl)phenylbenzonitrile

HRID 1713305
ノート
印刷プレビュー

反応式

HRID 1713305 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

HCID 674548124-(3-Hydroxypropylsulfanyl)phenylbenzonitrile収率 71.2%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ad5c31d107e24ae6804bfbd2b1c92f9e
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07795236B2

反応ノート

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