Ammonium Chloride → Ethanone, 1-(4-chloro-3-fluorophenyl)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

HRID 2279450노트

반응식

HRID 2279450 반응식
[Si:1]([O:8][CH2:9][C:10](N(OC)C)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][C:18]=1[F:25].[NH4+].[Cl-]>C1COCC1>[Si:1]([O:8][CH2:9][C:10]([C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[C:18]([F:25])[CH:19]=1)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 116010942-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylacetamideHCID 178505943HCID 178505943, 화합물

생성물 1

HCID 68294408Ethanone, 1-(4-chloro-3-fluorophenyl)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-수율 93.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of 60 (15.12 g, 64.79 mmol) and THF (50 mL) cooled to 0° C. was added dropwise (4-chloro-3-fluorophenyl)magnesium bromide (226.8 mL, 113.4 mmol) and the solution was stirred at 0° C. for 2 h. Saturated NH4Cl was added and the reaction was extracted with DCM. The organic layer was separated, dried, filtered and concentrated. The crude product was purified by passage through a SiO2 plug eluting with 5% EtOAc/hexane to afford 18.36 g (93.6%) of 2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanone (62).

후처리

  1. extractionthe reaction was extracted with DCM
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by passage through a SiO2 plug
  7. washeluting with 5% EtOAc/hexane

출처 및 근거

ORD 기록
ord-d5290904d5624326901fbd297282c949
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

반응 노트

불러오는 중…