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

HRID 1485979

반응식

HRID 1485979 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 552789582-chloro-3-fluoro-N-methylaniline수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1fa51c74e6004bcda821e70931dc7942
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422310B2

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