Bromine → 4-Bromo-1-(cyclopropylsulfanyl)-2-methylbenzene

HRID 70564ノート

反応式

HRID 70564 の反応式
[Br:1]Br.[CH:3]1([S:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[CH2:5][CH2:4]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C.[Cl-].[Na+].O>[Br:1][C:10]1[CH:11]=[CH:12][C:7]([S:6][CH:3]2[CH2:5][CH2:4]2)=[C:8]([CH3:13])[CH:9]=1

参加物

6

反応物 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 579565761-(Cyclopropylsulfanyl)-2-methylbenzene

生成物 1

HCID 584527214-Bromo-1-(cyclopropylsulfanyl)-2-methylbenzene収率 80%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

Bromine (0.42 mL) was added to a solution of 1-(cyclopropylsulfanyl)-2-methylbenzene (1.35 g) in acetic acid (10 mL) under ice-cooling, and the mixture was stirred at room temperature for 17 hours. The reaction solution was ice-cooled and a saturated sodium thiosulfate solution and brine were added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only) and the solvent was evaporated under reduced pressure. The precipitated solid was filtered and washed with hexane, after which the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only) to give the title compound as a pale yellow oil (1.59 g, 80%).

後処理

  1. temperaturecooling
  2. temperaturecooled
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane only) and the solvent
  8. customwas evaporated under reduced pressure
  9. filtrationThe precipitated solid was filtered
  10. washwashed with hexane
  11. customafter which the filtrate was evaporated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (hexane only)

出典と根拠

ORDレコード
ord-fba7a3f56f734ca2bb67d1a4d7a12f5c
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

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