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Oxalyl chloride → 2-Fluoro-N-(2-fluoro-3-hydroxy-6-methyl-phenyl)-5-(3-fluorophenyl)benzamide

HRID 1771627
ノート
印刷プレビュー

反応式

HRID 1771627 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(C(Cl)=O)=O.[NH2:24][C:25]1[C:26]([F:33])=[C:27]([OH:32])[CH:28]=[CH:29][C:30]=1[CH3:31].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C.C1COCC1.O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([NH:24][C:25]1[C:30]([CH3:31])=[CH:29][CH:28]=[C:27]([OH:32])[C:26]=1[F:33])=[O:6]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 463123323',4-Difluoro-[1,1'-biphenyl]-3-carboxylic acidHCID 894440343-Amino-2-fluoro-4-methylphenol

生成物 1

HCID 894436192-Fluoro-N-(2-fluoro-3-hydroxy-6-methyl-phenyl)-5-(3-fluorophenyl)benzamide収率 60%

試薬・触媒・溶媒 4

HCID 6228
Dimethylformamide
触媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of 2 fluoro-5-(3-fluorophenyl) benzoic acid (intermediate III(a)) (730 mg, 3.1 mmol, 1.1 eq) and (COCl)2 (1.1 g, 8.49 mmol, 3 eq) in DCM (20 mL) was added DMF (5 drops). The reaction mixture was stirred at 0° C. for 1h and then concentrated in vacuo. The residue obtained was dissolved in THF (5 mL) and added dropwise to a solution of 3-amino-2-fluoro-4-methyl-phenol (400 mg, 2.83 mmol, 1 eq) 25 and NaHCO3 (951 mg, 11.3 mmol, 4 eq) in THF (15 mL) at 0° C. After the addition, the reaction mixture was stirred at room temperature for 3h. The resulting mixture was poured into water and extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4) to give the title compound as a yellow solid (600 mg, 60%).

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. additionAfter the addition
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4)

出典と根拠

ORDレコード
ord-1fd639b3f6e84ca484a80f2b5fa67afa
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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