Dimethylformamide → 3-Bromo-4-methylbenzamide

HRID 70281

反応式

HRID 70281 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.C[N:19](C=O)C.[NH4+].[OH-]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH2:19])=[O:6]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 821303-Bromo-4-methylbenzoic acid

生成物 1

HCID 6810613-Bromo-4-methylbenzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a slurry of 3-bromo-4-methylbenzoic acid (2.53 g, 85% purity; 10 mmol) in CH2Cl2 (20 mL) at 0° C., under N2, was added oxalyl chloride (0.91 mL; 10.5 mmol), followed by dropwise addition of DMF (0.04 mL; 0.5 mmol). The mixture was stirred 5 min at 0° C., 15 min at rt, and then heated at reflux under N2 for 1 h. The mixture was cooled, and poured into NH4OH (30 mL; ca. 30% NH3). Precipitated solids were collected by filtration and purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless solid. LC/MS (method A) tR 2.05 min; m/z 214, 216 (M+H, Br isotopes).

後処理

  1. temperatureheated
  2. temperatureat reflux under N2 for 1 h
  3. temperatureThe mixture was cooled
  4. customPrecipitated solids
  5. filtrationwere collected by filtration
  6. custompurified by flash chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-0bc7b19fa9f24800958d5f2444e70ed5
出典データセット
uspto-grants-2014_09
特許番号
US08822518B2

関連ノート

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