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

HRID 1485979

反応式

HRID 1485979 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-1fa51c74e6004bcda821e70931dc7942
出典データセット
uspto-grants-2016_08
特許番号
US09422310B2

関連ノート

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