Oxalyl chloride → Benzoic acid, 2-chloro-6-nitro-, methyl ester

HRID 598086노트

반응식

HRID 598086 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=[O:5].[C:14](Cl)(=O)C(Cl)=O>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([O:6][CH3:14])=[O:5]

참가 물질

5

반응물 2

HCID 65578Oxalyl chlorideHCID 792872-Chloro-6-nitrobenzoic acid

생성물 1

HCID 603613Benzoic acid, 2-chloro-6-nitro-, methyl ester수율 95.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

To a suspension containing 3.0 g (15 mmol) of 2-chloro-6-nitrobenzoic acid in 150 ml of dichloromethane was added 2.8 g (22 mmol) of oxalyl chloride followed by 0.055 ml (0.75 mmol) of N,N-dimethylformamide. The reaction was allowed to stir at room temperature for 2 h, quenched with 50 ml of methanol and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 10% ethyl acetate/hexanes gave 3.1 g (9-7%) of product.

후처리

  1. customquenched with 50 ml of methanol
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationFiltration, removal of solvent and purification of the residue via biotage
  7. washeluting with 10% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-2037e4060daa427994f5bba795226983
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897607B2

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