Oxalyl chloride → 3-Bromo-4-chloro-5-nitrobenzonitrile

HRID 921605

反応式

HRID 921605 の反応式
C(Cl)(=O)C([Cl:4])=O.[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[C:15]=1O)[C:11]#[N:12]>CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[C:15]=1[Cl:4])[C:11]#[N:12]

参加物

4

反応物 2

HCID 65578Oxalyl chlorideHCID 3014048Benzonitrile, 3-bromo-4-hydroxy-5-nitro-

生成物 1

HCID 867084553-Bromo-4-chloro-5-nitrobenzonitrile収率 79.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

(I1C): DMF (2 mL) was cooled to −20° C. and treated gradually in dropwise manner with oxalyl chloride (0.216 mL, 2.469 mmol). After 10 min, a solution of 3-bromo-4-hydroxy-5-nitrobenzonitrile (200 mg, 0.823 mmol) in DMF (2 mL) was added slowly via syringe while maintaining internal temperature below −10° C. After addition, the mixture was allowed to warm to room temperature and then heated at 100° C. for 1.5 h. The reaction mixture was cooled and poured into ice-water; the solid was collected by filtration, rinsed with water and dried to give 172 mg of 3-bromo-4-chloro-5-nitrobenzonitrile as tan solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 8.13 (1H, d, J=1.76 Hz), 8.02 (1H, d, J=1.98 Hz)

後処理

  1. temperaturewhile maintaining internal temperature below −10° C
  2. additionAfter addition
  3. temperatureheated at 100° C. for 1.5 h
  4. temperatureThe reaction mixture was cooled
  5. filtrationthe solid was collected by filtration
  6. washrinsed with water
  7. customdried

出典と根拠

ORDレコード
ord-b19c6ff0f876488d9b8d97b30e24fe42
出典データセット
uspto-grants-2016_03
特許番号
US09273057B2

関連ノート

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