Ammonium Chloride → Tert-butyl 4-amino-2-fluorobenzoate

HRID 1861222

反応式

HRID 1861222 の反応式
[F:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:7]([O:6][C:4](=[O:5])[C:3]1[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][C:2]=1[F:1])([CH3:10])([CH3:8])[CH3:9]

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 10243388Tert-butyl 2-fluoro-4-nitrobenzoate

生成物 1

HCID 10058989Tert-butyl 4-amino-2-fluorobenzoate収率 99.9%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
95 °C

実験手順

Tert-butyl 2-fluoro-4-nitrobenzoate (24.2 g, 0.100 mol) was added to a warm (95° C.) solution of ammonium chloride (53.5 g, 1.00 mol), dissolved in ethanol (300 ml) and water (150 ml). Iron powder (325 mesh, 16.8 g, 0.300 mol) was added with stirring in small portions over ca. 1 h. The reaction mixture was stirred and heated at 95° C. for another 30 minutes and then filtered while still warm. The filter cake was washed thoroughly with excess ethanol. The filtrate and washings were diluted with water (1 L) and extracted with ether (3×150 ml). Combined ether extracts were washed with water and brine, dried (MgSO4), and evaporated to give the product as an off-white solid (21.1 g, 98%); mp 100-101° C. 1H NMR.

後処理

  1. stirringThe reaction mixture was stirred
  2. filtrationfiltered
  3. temperaturewhile still warm
  4. washThe filter cake was washed thoroughly with excess ethanol
  5. additionThe filtrate and washings were diluted with water (1 L)
  6. extractionextracted with ether (3×150 ml)
  7. washCombined ether extracts were washed with water and brine
  8. dry with materialdried (MgSO4)
  9. customevaporated

出典と根拠

ORDレコード
ord-26496dbeebe1456b81211f87c9bf64fb
出典データセット
uspto-grants-2003_03
特許番号
US06531470B1

関連ノート

読み込み中…