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

HRID 1258908ノート

反応式

HRID 1258908 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13](=[O:15])[CH3:14])=[C:11]([CH3:16])[N:10]=[N:9]2)=[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][CH2:14][C:13]([C:12]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]=[N:10][C:11]=1[CH3:16])=[O:15]

参加物

5

反応物 3

HCID 24408BromineHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 679549821-[3-(4-Fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-yl]-ethanone

生成物 1

HCID 885313122-Bromo-1-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-yl]-ethanone収率 68%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

A solution of 1-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-yl]-ethanone (3.62 g, 17 mmol) was dissolved in chloroform (28 mL) and acetic (0.5 mL) was heated to reflux and then a solution of bromine (0.89 mL, 17 mmol) in chloroform (9 mL) and heated under reflux for 2 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, 10 to 60% ethyl acetate in heptane) afforded the title compound (3.34 g, 68%) as an off white solid. MS: m/e=298.3/300.2 [M+H]+.

後処理

  1. temperatureto reflux
  2. temperatureunder reflux for 2 h
  3. additionwas poured onto ice-water
  4. extractionthe mixture extracted with dichloromethane
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by chromatography (silica, 10 to 60% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-115fcb597ca64cb89f8c1c6738b9b1f2
出典データセット
uspto-grants-2013_06
特許番号
US08466181B2

反応ノート

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