Sodium Carbonate → Isopropyl 2-(3-amino-2,4-difluoro-phenoxy)acetate

HRID 1771600ノート

反応式

HRID 1771600 の反応式
[NH2:1][C:2]1[C:3]([F:10])=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C([O-])([O-])=O.[Na+].[Na+].Br[CH2:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20]>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([F:10])=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][CH2:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 121593Isopropyl bromoacetateHCID 227559833-Amino-2,4-difluorophenol

生成物 1

HCID 89444213Isopropyl 2-(3-amino-2,4-difluoro-phenoxy)acetate収率 71%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 3-amino-2,4-difluoro-phenol (intermediate X(a)) (713 mg, 4.91 mmol, 1.0 eq) in DMF (20 mL) was added Na2CO3 (1.56 g, 14.8 mmol, 3.0 eq). The resulting mixture was stirred at room temperature for 35 min, then isopropyl bromoacetate (1.07 g, 5.90 mmol, 1.2 eq) was added and the reaction stirred at room temperature overnight. The reaction was diluted with water then extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by chromatography (EtOAc:petroleum ether, 0:1 to 1:6) to give the title compound (intermediate IV(b)) as an oil (850 mg, 71%).

後処理

  1. stirringthe reaction stirred at room temperature overnight
  2. extractionthen extracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography (EtOAc:petroleum ether, 0:1 to 1:6)

出典と根拠

ORDレコード
ord-21d85328e4794c0fb05cd977bbea6f2f
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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