Methyl chloroacetate → 7-Bromo-5-fluorobenzofuran-2-carboxylic acid

HRID 383847

反応式

HRID 383847 の反応式
Cl[CH2:2][C:3]([O:5]C)=[O:4].[Br:7][C:8]1[C:9]([OH:17])=[C:10]([CH:13]=[C:14]([F:16])[CH:15]=1)[CH:11]=O.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>O1CCCC1.O>[Br:7][C:8]1[C:9]2[O:17][C:2]([C:3]([OH:5])=[O:4])=[CH:11][C:10]=2[CH:13]=[C:14]([F:16])[CH:15]=1

参加物

7

反応物 4

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 231489553-Bromo-5-fluoro-2-hydroxybenzaldehyde

生成物 1

HCID 179827017-Bromo-5-fluorobenzofuran-2-carboxylic acid収率 63%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
130 °C

実験手順

Methyl chloroacetate (7.6 mL, 86.8 mmol) was added to a mixture of 3-bromo-5-fluoro-2-hydroxy-benzaldehyde (9.5 g, 43.4 mmol), tetra-N-butyl-ammonium iodide (1.6 g, 4.34 mmol) and anhydrous potassium carbonate (24 g, 174 mmol). The reaction mixture was heated at 130° C. for 4 h, cooled to 0° C., diluted with tetrahydrofuran (100 mL) and then potassium hydroxide (17 g, 303 mmol) in water (100 mL). The mixture was stirred at rt for 18 h and then, concentrated under reduced pressure. The residue was acidified with HCl and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; toluene/EtOAc, 40/1) to give 7.0 g (63%) of the product.

後処理

  1. temperaturecooled to 0° C.
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude compound was purified by flash chromatography (SiO2; toluene/EtOAc, 40/1)

出典と根拠

ORDレコード
ord-ad46f0e3149443759274e90b78c14389
出典データセット
uspto-grants-2013_02
特許番号
US08367676B2

関連ノート

読み込み中…