Dimethyl Sulfate → 5-Bromo-2-chloro-3,4-dimethoxybenzaldehyde

HRID 576383ノート

反応式

HRID 576383 の反応式
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([O:11][CH3:12])[C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:14]OS(OC)(=O)=O>C1COCC1>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([O:11][CH3:12])[C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=[O:8]

参加物

4

反応物 2

HCID 6497Dimethyl SulfateHCID 867140745-Bromo-2-chloro-4-hydroxy-3-methoxybenzaldehyde

生成物 1

HCID 867140735-Bromo-2-chloro-3,4-dimethoxybenzaldehyde収率 70.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

To the mixture of aldehyde 156 (15.0 g, 56.5 mmol) in THF (300 mL) were added dimethylsulfate (7.0 mL, 73.5 mmol) and LiOH monohydrate (3.1 g, 73.5 mmol). The mixture was stirred for 3 hours at 65° C. The mixture was cooled to r.t. and filtered to remove insoluble materials through celite. The filtrate was extracted with EtOAc/aq. 50% NaCl solution (200 mL/500 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 157 (11.1 g, 70%).

後処理

  1. temperatureThe mixture was cooled to r.t.
  2. filtrationfiltered
  3. customto remove insoluble materials through celite
  4. extractionThe filtrate was extracted with EtOAc/aq
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-cf0610b973134597be3c52ea8dfc61d5
出典データセット
uspto-grants-2015_05
特許番号
US09034921B2

反応ノート

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