Methyl iodide → Benzoic acid, 2-bromo-5-fluoro-, methyl ester

HRID 84935

反応式

HRID 84935 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:12][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:2]=1[Br:1]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27781812-Bromo-5-fluorobenzoic acid

生成物 1

HCID 138875Benzoic acid, 2-bromo-5-fluoro-, methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-bromo-5-fluorobenzoic acid (7.92 g, 36.2 mmol) in N,N-dimethylformamide (75 mL) was added potassium carbonate (6.91 g, 50.0 mmol) as a solid in one portion at room temperature. The mixture was stirred for 5 minutes and iodomethane (6.39 g, 45.0 mmol) was added in one portion. The mixture was stirred at ambient temperature for 22 hours. The reaction mixture was partitioned between ethyl acetate and water. The aqueous portion was extracted with additional ethyl acetate (3×) and the combined organic extracts were washed successively with 10% potassium carbonate solution, water and brine. The organic portion was dried (Na2SO4) and concentrated to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.87 (s, 3H) 7.41 (td, J=8.56, 3.22 Hz, 1H) 7.65 (dd, J=8.99, 3.22 Hz, 1H) 7.81 (dd, J=9.16, 5.09 Hz, 1H); MS (+DCI/NH3) m/z 250.0 [M+NH4]+.

後処理

  1. stirringThe mixture was stirred at ambient temperature for 22 hours
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous portion was extracted with additional ethyl acetate (3×)
  4. washthe combined organic extracts were washed successively with 10% potassium carbonate solution, water and brine
  5. dry with materialThe organic portion was dried (Na2SO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-5de3b6ba492440bb930031c699186b10
出典データセット
uspto-grants-2014_09
特許番号
US08846951B2

関連ノート

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