Sodium Cyanide → Ethyl 3,6-dichloro-2-(cyanomethyl)benzoate

HRID 577499ノート

反応式

HRID 577499 の反応式
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([Cl:18])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(OC)(C)(C)C>O.CS(C)=O>[Cl:17][C:16]1[C:6]([CH2:5][C:1]#[N:2])=[C:7]([C:13]([Cl:18])=[CH:14][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

参加物

6

反応物 3

HCID 8929Sodium CyanideHCID 15413tert-Butyl methyl etherHCID 86723724Ethyl 2-(bromomethyl)-3,6-dichlorobenzoate

生成物 1

HCID 86723725Ethyl 3,6-dichloro-2-(cyanomethyl)benzoate収率 56.4%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒2 回

実験手順

A solution of sodium cyanide (75.12 g, 1.53 mol) in water (300 mL) was added dropwise to a solution of ethyl 2-(bromomethyl)-3,6-dichlorobenzoate (253c, 320 g, 1.03 mol) in dimethylsulfoxide (2.4 L) at room temperature. The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was poured into a mixture of water (4 L) and methyl tert-butyl ether (2 L), and the layers separated. The organic layer was washed with water (2 L) and with saturated aqueous sodium chloride solution (2 L), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography (eluting with 30:1 petroleum ether/ethyl acetate), affording ethyl 3,6-dichloro-2-(cyanomethyl)benzoate (253d, 150 g, ˜75% pure, 47% yield) as a yellow oil.

後処理

  1. customthe layers separated
  2. washThe organic layer was washed with water (2 L) and with saturated aqueous sodium chloride solution (2 L)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (eluting with 30:1 petroleum ether/ethyl acetate)

出典と根拠

ORDレコード
ord-f81b5bb9a6514523b2397a62b1b8ae70
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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