Dimethylformamide → 2-(4-Bromo-2-fluoro-phenoxy)-2-methyl-propionic acid methyl ester

HRID 1453030ノート

反応式

HRID 1453030 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.Br[CH:11]([CH2:15]C)[C:12]([O-])=O.[C:17]([O-:20])([O-])=[O:18].[K+].[K+].[CH3:23]N(C=O)C>>[CH3:23][O:20][C:17](=[O:18])[C:11]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:9])([CH3:15])[CH3:12]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1523172-BromobutyrateHCID 27249814-Bromo-2-fluorophenol

生成物 1

HCID 575272722-(4-Bromo-2-fluoro-phenoxy)-2-methyl-propionic acid methyl ester収率 77%

反応条件

温度
100 °C

実験手順

To a solution of 4-Bromo-2-fluorophenol (1 g, 5.24 mmol) and methyl □-bromobutyrate (1.89 g, 10.47 mmol) in DMF (20 mL) was added K2CO3 (3.6 g, 26 mmol). The resultant slurry was heated to 100° C. under argon for 12 h. DMF was evaporate and residue partitioned between EtOAC and 1N HCl. The organic layer was washed with H2O, and brine then dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (10% EtOAc in hexanes) to provide the desired product (1.17 g, 77%) as a white solid. 1H NMR (CDCl3) δ: 1.57 (s, 6H), 3.79 (s, 3H),), 6.86 (t, J=8.7, 1H), 7.12-7.16 (m, 1H), 7.23-7.27 (m, 1H).

後処理

  1. customDMF was evaporate
  2. customresidue partitioned between EtOAC and 1N HCl
  3. washThe organic layer was washed with H2O, and brine
  4. dry with materialthen dried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash column chromatography (10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-f4cdaa5989db4fbaaf844d15ffcd3686
出典データセット
uspto-grants-2009_01
特許番号
US07473790B2

反応ノート

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