1-Methylimidazole → 1-(3-Chloro-4-fluorophenyl)propan-2-one

HRID 514101

반응식

HRID 514101 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:13]N1C=CN=C1>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](=[O:12])[CH3:13])[CH:5]=[CH:6][C:7]=1[F:8]

참가 물질

4

반응물 2

HCID 13901-MethylimidazoleHCID 27737212-(3-Chloro-4-fluorophenyl)acetic acid

생성물 1

HCID 552735661-(3-Chloro-4-fluorophenyl)propan-2-one수율 79%

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

To a solution of 2-(3-chloro-4-fluorophenyl)acetic acid (18.46 g, 97.89 mmol) in acetic anhydride (463 mL) was added N-methylimidazole (3.9 mL) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution and organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a colorless oil (14.5 g, 79%). 1H NMR (400 MHz, CDCl3) δ 7.23 (dd, J=6.9, 2.1 Hz, 1H), 7.14-7.00 (m, 2H), 3.66 (s, 2H), 2.19 (s, 3H).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution and organic layer
  2. concentrationwas concentrated
  3. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-6c2c69c9e4604669bf78354308ba7cf5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102614B2

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