Aluminium lithium hydride → 2-chloro-3-fluoro-N-methylaniline

HRID 661664

反応式

HRID 661664 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=1[NH:15][CH:16]=O>C1COCC1>[CH3:16][NH:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:8]=1[Cl:7]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 57346568N-(2-Chloro-3-fluorophenyl)formamide

生成物 1

HCID 552789582-chloro-3-fluoro-N-methylaniline収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred suspension of 95% lithium aluminum hydride (2.19 g, 58 mmol) in anhydrous THF (10 mL) at 0° C., was added dropwise a solution of N-(2-chloro-3-fluoro phenyl)-formamide (2.3 g, 13.2 mmol) in anhydrous THF (20 mL). The reaction mixture was allowed to slowly warm to room temperature and was stirred for a further 40 mins. The mixture was cooled to 0° C. and was quenched via the sequential addition of water (4 mL), 15% aq. NaOH (2 mL), then water (4 mL). Organics were extracted into a mixture of 3:1 DCM: IPA (100 mL) and washed with water (50 mL). The organic layer was separated and dried over MgSO4. Filtration then concentration in vacuo gave N-methyl-2-chloro-3-fluoroaniline 29-1 (2.07 g, 99%) as a yellow oil. MS (M+H)+: 160.1, tR=2.21 min (method 1).

後処理

  1. temperatureThe mixture was cooled to 0° C.
  2. customwas quenched via the sequential addition of water (4 mL), 15% aq. NaOH (2 mL)
  3. extractionOrganics were extracted into a mixture of 3:1 DCM
  4. washIPA (100 mL) and washed with water (50 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationFiltration
  8. concentrationconcentration in vacuo

出典と根拠

ORDレコード
ord-5f711e4301f149ecaf6acf4f19b158cf
出典データセット
uspto-grants-2011_12
特許番号
US08084614B2

関連ノート

読み込み中…