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

HRID 1771600노트

반응식

HRID 1771600 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-21d85328e4794c0fb05cd977bbea6f2f
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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