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

HRID 56620

反応式

HRID 56620 の反応式
[Cl-].[NH4+].[F:3][C:4]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>C(O)C.O.[Fe]>[NH2:17][C:15]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:7])=[C:4]([F:3])[CH:16]=1

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

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

A solution of 1.109 g (20.73 mmol, 10 eq.) of ammonium chloride in 6.25 ml of ethanol and 3.125 ml of water was heated to 95° C., and 500 mg (2.07 mmol) of tert-butyl 2-fluoro-4-nitrobenzoate were added. 347 mg (6.22 mmol, 3 eq.) of iron powder were added in small portions over 1 h. The reaction mixture was then stirred at 95° C. for 30 min, and the hot mixture was then filtered through kieselguhr. The filter cake was washed with ethanol and the filtrate was freed from ethanol under reduced pressure. The aqueous phase was extracted three times with in each case 20 ml of diethyl ether. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude product was purified by normal phase chromatography (mobile phase: cyclohexane/ethyl acetate 30%-50% mixtures). Yield: 280 mg (51% of theory).

後処理

  1. filtrationthe hot mixture was then filtered through kieselguhr
  2. washThe filter cake was washed with ethanol
  3. extractionThe aqueous phase was extracted three times with in each case 20 ml of diethyl ether
  4. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (sodium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by normal phase chromatography (mobile phase: cyclohexane/ethyl acetate 30%-50% mixtures)

出典と根拠

ORDレコード
ord-7eb1dd37a4784e0c9f90e7e5048e134d
出典データセット
uspto-grants-2016_09
特許番号
US09434690B2

関連ノート

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