Dimethyl Sulfate → 5-Bromo-2-chloro-4-methoxybenzonitrile

HRID 46228

反応式

HRID 46228 の反応式
[Br:1][C:2]1[C:3]([OH:11])=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8].S(OC)(O[CH3:16])(=O)=O.O.[OH-].[Li+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[C:3]([O:11][CH3:16])=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8]

参加物

6

反応物 3

HCID 6497Dimethyl SulfateHCID 168937Lithium hydroxide, monohydrateHCID 533304525-Bromo-2-chloro-4-hydroxybenzonitrile2 回

生成物 1

HCID 672873335-Bromo-2-chloro-4-methoxybenzonitrile収率 76%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 5-bromo-2-chloro-4-hyroxybenzonitrile (compound 87, 38.1 g, 164 mmol), dimethyl sulfate (20.1 mL, 213 mmol), and lithium hydroxide monohydrate (8.93 g, 213 mmol) in THF (500 mL) was refluxed overnight. The mixture was cooled to ambient temperature and then diluted with EtOAc. The EtOAc solution was washed with water and brine prior to drying over anhydrous MgSO4. Filtration and removal of the voletiles under reduced pressure left the crude product which was purified by column chromatography (5-40% EtOAC/hexanes) to yield 5-bromo-2-chloro-4-methoxybenzonitrile (30.7 g, 76%) as a white solid.

後処理

  1. temperaturewas refluxed overnight
  2. washThe EtOAc solution was washed with water and brine
  3. dry with materialto drying over anhydrous MgSO4
  4. filtrationFiltration and removal of the voletiles under reduced pressure
  5. waitleft the crude product which
  6. customwas purified by column chromatography (5-40% EtOAC/hexanes)

出典と根拠

ORDレコード
ord-d8a489cf90a04a668a483a1680f139a3
出典データセット
uspto-grants-2013_09
特許番号
US08541380B2

関連ノート

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