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Ethyl bromoacetate → Ethyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl) phenyl]methylamino]phenoxy]acetate

HRID 1771608
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HRID 1771608 반응식
[F:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH:11]=2)=[C:6]([F:23])[CH:5]=[CH:4][C:3]=1[OH:24].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CC(C)=O>[F:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH:11]=2)=[C:6]([F:23])[CH:5]=[CH:4][C:3]=1[O:24][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 894442752,4-Difluoro-3-[[3-(3-fluorophenyl)phenyl]methylamino]phenol

생성물 1

HCID 89444317Ethyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl) phenyl]methylamino]phenoxy]acetate수율 86%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a stirred solution of 2,4-difluoro-3-[[3-(3-fluorophenyl)phenyl]methylamino]phenol (250 mg, 0.76 mmol, 1.0 eq) in acetone (3 mL) was added Cs2CO3 (297 mg, 0.912 mmol, 1.2 eq). The resulting mixture was stirred for 40 min at room temperature then ethyl bromoacetate (139.4 mg, 0.84 mmol, 1.1 eq) was added. The resulting mixture was stirred overnight then partitioned against water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether:EtOAc 1:0 to 20:1) to give the title compound as an oil (270 mg, 86%).

후처리

  1. stirringThe resulting mixture was stirred overnight
  2. customthen partitioned against water
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography (petroleum ether:EtOAc 1:0 to 20:1)

출처 및 근거

ORD 기록
ord-f5026a771f6c4386937b1928f9d7e716
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249085B2

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