(o-Chlorophenyl)acetonitrile → 2-Biphenylacetonitrile

HRID 382100

反応式

HRID 382100 の反応式
[OH-].[OH-].[C:3]1([B+2])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F-].[K+].Cl[C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[CH2:15][C:16]#[N:17]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C1COCC1>[C:16]([CH2:15][C:14]1[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)#[N:17]

参加物

7

反応物 3

HCID 76112(o-Chlorophenyl)acetonitrileHCID 522689Potassium FluorideHCID 178419127HCID 178419127、化合物

生成物 1

HCID 3341012-Biphenylacetonitrile収率 92.1%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 27342152-(Di-tert-butylphosphino)biphenyl触媒HCID 8028Tetrahydrofuran溶媒

実験手順

An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol %), phenylboron dihydroxide (183 mg. 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-chlorobenzyl cyanide (152 mg, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with 1.0 M NaOH (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 178 mg (92%) of the title compound.

後処理

  1. customAn oven dried resealable Schlenk tube
  2. customwas evacuated
  3. customThe tube was evacuated
  4. additionwere added through a rubber septum
  5. customhad been completely consumed
  6. additionThe reaction mixture was then diluted with ether (30 mL)
  7. additionpoured into a separatory funnel
  8. washThe mixture was washed with 1.0 M NaOH (20 mL)
  9. extractionthe aqueous layer was extracted with ether (20 mL)
  10. washThe combined organic layers were washed with brine (20 mL)
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe crude material was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-70312105dcc04818b1d5a943b306a257
出典データセット
uspto-grants-2001_10
特許番号
US06307087B1

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