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

HRID 1771608
ノート
印刷プレビュー

反応式

HRID 1771608 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-f5026a771f6c4386937b1928f9d7e716
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09249085B2

反応ノート

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