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

HRID 577499노트

반응식

HRID 577499 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f81b5bb9a6514523b2397a62b1b8ae70
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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