Bromoacetyl bromide → 5-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester

HRID 1914568

反応式

HRID 1914568 の反応式
[Cl-].[Cl-].[Cl-].[Al+3].[Br:5][CH2:6][C:7](Br)=[O:8].[CH3:10][O:11][C:12]([C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)=[O:13]>C(Cl)Cl>[CH3:10][O:11][C:12]([C:14]1[CH:18]=[C:17]([C:7](=[O:8])[CH2:6][Br:5])[S:16][CH:15]=1)=[O:13]

参加物

5

反応物 3

HCID 61147Bromoacetyl bromideHCID 574151Methyl 3-thiophenecarboxylateHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 539045465-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester収率 39.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

Aluminium trichloride (4.26 g, 32.0 mmol) was dissolved in DCM (15 mL) and cooled to 0° C. Bromoacetyl bromide (1.78 mL, 20.4 mmol) was added slowly as a solution in DCM (7 mL) and stirred at 0° C. for 1 hour. Thiophene-3-carboxylic acid methyl ester (2.89 g, 20.4 mmol) was then added slowly as a solution in DCM (15 mL) and the mixture stirred overnight warming to room temperature. The mixture was poured into ice/water and extracted with DCM (×2) then the organics were washed with water, dried over sodium sulfate, filtered and evaporated. The residue was purified by chromatography on a 50 g silica II cartridge, eluting with 2:1 pentane:DCM to neat DCM, to give the title compound as a white solid (2.1 g). 1H NMR (400 MHz, CHCl3-d): δ 8.4 (d, 1H), 8.2 (d, 1H), 4.4 (s, 2H), 3.9 (s, 3H).

後処理

  1. stirringthe mixture stirred overnight
  2. temperaturewarming to room temperature
  3. extractionextracted with DCM (×2)
  4. washthe organics were washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on a 50 g silica II cartridge
  9. washeluting with 2:1 pentane

出典と根拠

ORDレコード
ord-c059964cac1b4544888d4398a7c542dc
出典データセット
uspto-grants-2013_12
特許番号
US08614209B2

関連ノート

読み込み中…