Acetone → 1-Bromo-3-(3-fluoro-2-methyl-phenyl)-propan-2-one

HRID 1963090노트

반응식

HRID 1963090 반응식
[Br:1]Br.[F:3][C:4]1[C:5]([CH3:14])=[C:6]([CH2:10][C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][CH:9]=1.Br.CC(C)=O>C(O)(=O)C>[Br:1][CH2:12][C:11](=[O:13])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([F:3])[C:5]=1[CH3:14]

참가 물질

6

반응물 4

HCID 180AcetoneHCID 260Hydrogen BromideHCID 24408BromineHCID 247216491-(3-Fluoro-2-methylphenyl)propan-2-one

생성물 1

HCID 866706671-Bromo-3-(3-fluoro-2-methyl-phenyl)-propan-2-one수율 69.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매3회

실험 절차

Analogously to the procedure described in H. Y. Choi et al., Org. Lett. 5 (2003), 411, a solution of bromine (8.46 g, 52.95 mmol) in acetic acid (12 ml) was added at 0° C. to a solution of 1-(3-fluoro-2-methyl-phenyl)-propan-2-one (4.00 g, 24.07 mmol) in acetic acid (4 ml) and a 33% solution of hydrogen bromide in acetic acid (4 ml). The mixture was warmed to room temperature and stirred for 12 h. Then acetone was added and the mixture was stirred for 24 h. After evaporation under reduced pressure, the residue was extracted several times with DCM. The combined extracts were dried over sodium sulfate and evaporated to dryness. The residue was purified by preparative HPLC to give 4.10 g of the title compound as an oil.

후처리

  1. stirringthe mixture was stirred for 24 h
  2. customAfter evaporation under reduced pressure
  3. extractionthe residue was extracted several times with DCM
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-e995ad2801044255bf33f9df0d108906
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415336B2

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