Water → 5-bromo-6-chloro-1H-indole-3-carbaldehyde

HRID 338215

反応式

HRID 338215 の反応式
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[Cl:16])[NH:12][CH:11]=[CH:10]2.[OH-].[Na+].O.CN([CH:23]=[O:24])C>>[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[Cl:16])[NH:12][CH:11]=[C:10]2[CH:23]=[O:24]

参加物

6

反応物 5

HCID 962WaterHCID 6228Dimethylformamide2 回HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 144196195-Bromo-6-chloro-1H-indole

生成物 1

HCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehyde収率 90%

実験手順

A round-bottom flask was charged with DMF (54 mL). Phosphorus oxychloride (6.21 mL, 66.8 mmol) was added dropwise over 5 minutes, and the reaction mixture was stirred at room temperature for an additional 5 minutes. A solution of 5-bromo-6-chloro-1H-indole (7700 mg, 33.41 mmol) in DMF (7 mL) was added dropwise to the reaction mixture, which caused a precipitate to form. The reaction mixture was then heated to 95° C. for 25 minutes. The reaction mixture was treated with 1N aqueous sodium hydroxide (170 mL) and water (170 mL). The reaction mixture was stirred at 95° C. for 11 minutes. The reaction mixture was cooled to 0° C., and the solids were collected by filtration. The solids were washed with water (50 mL) and diethyl ether (50 mL) and dried in vacuo for 16 hours at 65° C. to afford the title compound (7.77 g, 90%) as a tan solid. MS (AP+) 257.9 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 9.93 (s, 1H), 8.40 (s, 1H), 8.38 (s, 1H), 7.80 (s, 1H).

後処理

  1. customto form
  2. temperatureThe reaction mixture was then heated to 95° C. for 25 minutes
  3. stirringThe reaction mixture was stirred at 95° C. for 11 minutes
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. filtrationthe solids were collected by filtration
  6. washThe solids were washed with water (50 mL) and diethyl ether (50 mL)
  7. customdried in vacuo for 16 hours at 65° C.

出典と根拠

ORDレコード
ord-f464c0b1052e4b14af58529730b22da5
出典データセット
uspto-grants-2014_11
特許番号
US08889730B2

関連ノート

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