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Bromine → 2-Bromo-1-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]-triazol-4-yl]-ethanone

HRID 1258877
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HRID 1258877 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[C:14](=[O:16])[CH3:15])=[CH:4][CH:3]=1.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[Br:41]Br>C(Cl)(Cl)Cl>[Br:41][CH2:15][C:14]([C:9]1[N:10]([CH3:13])[N:11]=[N:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:16]
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참가 물질

5

반응물 3

HCID 24408Bromine2회HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 679548121-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]-triazol-4-yl]-ethanone

생성물 1

HCID 885313192-Bromo-1-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]-triazol-4-yl]-ethanone수율 63.7%

시약·촉매·용매 1

HCID 6212Chloroform
용매
2회

실험 절차

A solution of 1-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-ethanone (4.02 g, 18.34 mmol) was dissolved in chloroform (18 mL) and acetic (0.36 mL) was heated to reflux and then a solution of bromine (1.04 mL, 20.17 mmol) in chloroform (9 mL) was added dropwise within 10 min at and after 1 h bromine (0.10 mL, 2.02 mmol) was added and heated under reflux for 1 h. After cooling to room temperature the mixture was poured onto ice-water and the mixture extracted with dichloromethane. The combined organic extracts were washed with water, brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (3.48 g, 63%) as a light red solid. MS: m/e=298.1/300.1 [M+H]+.

후처리

  1. temperatureto reflux
  2. additionwas added
  3. temperatureheated
  4. temperatureunder reflux for 1 h
  5. additionwas poured onto ice-water
  6. extractionthe mixture extracted with dichloromethane
  7. washThe combined organic extracts were washed with water, brine
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-85cf64cd6d594af2b2f704d94cd92c96
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08466181B2

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