Acetyl chloride → 1-(4-Bromo-5-chloro-2-hydroxyphenyl)ethanone

HRID 626832노트

반응식

HRID 626832 반응식
[Br:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[Cl:10].[C:11](Cl)(=[O:13])[CH3:12].[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[Br:1][C:2]1[C:3]([Cl:10])=[CH:4][C:5]([C:11](=[O:13])[CH3:12])=[C:6]([OH:8])[CH:7]=1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 242120812-Bromo-1-chloro-4-methoxybenzene

생성물 1

HCID 595641771-(4-Bromo-5-chloro-2-hydroxyphenyl)ethanone수율 99.3%

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매

실험 절차

The 2-bromo-1-chloro-4-methoxybenzene (25.0 g, 113 mmol) [Oakwood cat#035670] was dissolved in carbon disulfide (250 mL), and the acetyl chloride (12 mL, 170 mmol) and aluminum trichloride (37.6 g, 282 mmol) were added. The reaction was heated to reflux and monitored by LC/MS. After heating for 1 h, the reaction became two layers. The reaction allowed to cool to room temperature and poured over ice. The slurry was extracted with ethyl acetate 3×, the combined organic layer was washed with brine, dried over magnesium sulfate and concentrated to give 1-(4-bromo-5-chloro-2-hydroxyphenyl)ethanone as a solid (28.0 g, 99%). 1H NMR (300 MHz, CDCl3) δ 12.12 (s, 1H), 7.78 (s, 1H), 7.31 (s, 1H), 2.62 (s, 3H).

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. temperatureAfter heating for 1 h
  4. additionpoured over ice
  5. extractionThe slurry was extracted with ethyl acetate 3×
  6. washthe combined organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f0f7c87820114e84b606c4a4a374221e
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309251B2

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