2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → Tert-butyl [4-(benzyloxy)-2-cyanophenyl]acetate

HRID 1850726ノート

反応式

HRID 1850726 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](Br)=[C:13]([CH:16]=1)[C:14]#[N:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[C:19]([O:23][C:24](=[O:27])[CH2:25][Zn+])([CH3:22])([CH3:21])[CH3:20].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1COCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:25][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:27])=[C:13]([C:14]#[N:15])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 121019865-(Benzyloxy)-2-bromobenzonitrileHCID 178451183HCID 178451183、化合物

生成物 1

HCID 86711182Tert-butyl [4-(benzyloxy)-2-cyanophenyl]acetate

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of 5-(benzyloxy)-2-bromobenzonitrile (0.73 g, 2.53 mmol) in THF (10 ml) was added 2-tert-butoxy-2-oxoethylzinc chloride (10.13 ml, 5.07 mmol). Nitrogen gas bubbled through the mixture for 10 min. then Pd2(dba)3 (0.116 g, 0.127 mmol) and X-PHOS (0.121 g, 0.253 mmol) were added and the resulting mixture heated at 60° C. for 50 min. The mixture was cooled, diluted with ethyl acetate (20 mL), washed with aqueous ammonium chloride (saturated, 1×15 mL), dried over MgSO4, filtered and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 50M, using a gradient eluant of EtOAc/Hexane (0-15%) to afford the title compound. LC/MS (m/z): 346 (M+H)+.

後処理

  1. customNitrogen gas bubbled through the mixture for 10 min.
  2. temperatureThe mixture was cooled
  3. washwashed with aqueous ammonium chloride (saturated, 1×15 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel Biotage 50M

出典と根拠

ORDレコード
ord-a34406a7d187478e80631547db9fca1d
出典データセット
uspto-grants-2015_02
特許番号
US08957062B2

反応ノート

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