Iodoethane → Ethyl 7-bromo-5-fluorobenzofuran-2-carboxylate

HRID 383848

反応式

HRID 383848 の反応式
[CH2:1](I)[CH3:2].[Br:4][C:5]1[C:13]2[O:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=2[CH:8]=[C:7]([F:17])[CH:6]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:4][C:5]1[C:13]2[O:12][C:11]([C:14]([O:16][CH2:1][CH3:2])=[O:15])=[CH:10][C:9]=2[CH:8]=[C:7]([F:17])[CH:6]=1

参加物

5

反応物 3

HCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 179827017-Bromo-5-fluorobenzofuran-2-carboxylic acid

生成物 1

HCID 59636759Ethyl 7-bromo-5-fluorobenzofuran-2-carboxylate収率 90.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

Ethyl iodide (4.6 ml, 57.2 mmol) was added to a mixture of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid (3.7 g, 14.3 mmol) and sodium bicarbonate (4.8 g, 57.2 mmol) in anhydrous dimethylformamide (40 mL). The mixture was heated at 55° C. for 18 h, cooled to rt, quenched with water (20 mL) and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1) to give 3.7 g (90%) of the product.

後処理

  1. temperaturecooled to rt
  2. customquenched with water (20 mL)
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1)

出典と根拠

ORDレコード
ord-336d4b8ed6594011bc6c0c7e2af2fd21
出典データセット
uspto-grants-2013_02
特許番号
US08367676B2

関連ノート

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