Sodium Hydroxide → 5-Bromo-7-fluoro-1-benzofuran-2-carboxylic acid

HRID 525198ノート

反応式

HRID 525198 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]=O)[C:5]([O:10][CH2:11][C:12]([OH:14])=[O:13])=[C:4]([F:15])[CH:3]=1.C([O-])(=O)C.[Na+].[OH-].[Na+]>C(OC(=O)C)(=O)C.C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([F:15])[C:5]2[O:10][C:11]([C:12]([OH:14])=[O:13])=[CH:8][C:6]=2[CH:7]=1

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 86674830[(4-bromo-2-fluoro-6-formylphenyl)oxy]acetic Acid

生成物 1

HCID 623792185-Bromo-7-fluoro-1-benzofuran-2-carboxylic acid収率 48%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 7918Acetic Anhydride溶媒

実験手順

A solution of [(4-bromo-2-fluoro-6-formylphenyl)oxy]acetic acid (3.79 mmol) in acetic anhydride (10 mL) was treated with sodium acetate (11.37 mmol). The resulting solution was heated to reflux and stirred overnight. The brown reaction solution was allowed to cool to room temperature, and was diluted with toluene (10 mL). The solution was then treated with 1N aq NaOH (20 mL) and was stirred at room temperature for 30 min. The solution was then further diluted with water (50 mL) and was extracted using hexanes. The aqueous phase was then acidifed to pH˜1 using 1N aq HCl, and was extracted with ethyl acetate. The ethyl acetate layers were combined, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide the title compound (0.47 g, 48% yield) which was used without further purification. MS(ES)+ m/e 258.5, 260.7 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.88 (d, J=1.77 Hz, 1H) 7.75 (dd, J=10.36, 1.77 Hz, 1H) 7.69 (d, J=2.53 Hz, 1H).

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. stirringwas stirred at room temperature for 30 min
  4. extractionwas extracted
  5. extractionwas extracted with ethyl acetate
  6. washwashed with saturated aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-43db7d4d553d48ea896d498ba12cbd0b
出典データセット
uspto-grants-2016_05
特許番号
US09340529B2

反応ノート

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