p-Bromoacetophenone → 2-(4-Bromophenyl)propan-2-ol

HRID 717133

반응식

HRID 717133 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][Mg]Br>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])([CH3:11])[CH3:9])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 7466p-BromoacetophenoneHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 126819202-(4-Bromophenyl)propan-2-ol수율 99.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-50 °C

실험 절차

1-(4-Bromophenyl)ethanone (9.25 g, 46.5 mmol) was dissolved in tetrahydrofuran (200 mL). The solution was cooled in a −50° C. bath. Methylmagnesium bromide (3M in ether, 46.5 mL, 139 mmol) was added over a 15 min period. The reaction was allowed to warm to room temperature and then stirred for 20 h. The reaction was quenched with saturated ammonium chloride and then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated to give an oil. The oil was purified on a silica gel column (0-20% ethyl acetate in hexanes) to give the product a colorless oil (9.1 g, 46.2 mmol, 91% yield). MS (ESI) m/z 197.1 [M]+, 199.1 [M+2]+.

후처리

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe oil was purified on a silica gel column (0-20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-86522330519141088ca8b4867b553901
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193692B2

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