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

HRID 598086ノート

反応式

HRID 598086 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2037e4060daa427994f5bba795226983
出典データセット
uspto-grants-2011_03
特許番号
US07897607B2

反応ノート

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