Potassium Carbonate → Ethyl 4-(4-cyano-2-fluorophenoxy)butanoate

HRID 219890

反応式

HRID 219890 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].Br[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([O:10][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:2]([F:1])[CH:3]=1)#[N:6]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 27829443-Fluoro-4-hydroxybenzonitrile

生成物 1

HCID 67529348Ethyl 4-(4-cyano-2-fluorophenoxy)butanoate収率 97.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

3-fluoro-4-hydroxybenzonitrile (ABCR F03756F.AB, 2 g; 14.59 mmol; 1 eq.) was dissolved in DMF (40 mL). Then ethyl 4-bromobutyrate (4.27 g; 21.88 mmol; 1.50 eq.) and potassium carbonate (3.02 g; 21.88 mmol; 1.50 eq.) were added to the reaction mixture and it was heated to 80° C. for 2 hours. The reaction mixture was cooled to RT and diluted with EtOAc. The organic layer was washed with water (3×), brine, dried over MgSO4 and concentrated affording the title compound as a yellow solid (3.56 g, 97%). 1H NMR (DMSO-d6, 300 MHz) δ 7.86-7.83 (d, J=11.43 Hz, 1H), 7.68-7.66 (d, J=8.73 Hz, 1H), 7.37-7.32 (m, 1H), 4.20-4.03 (m, 4H), 2.46-2.44 (m, 2H), 2.03-1.99 (m, 2H), 1.19-1.15 (t, J=6.62 Hz, 3H). HPLC (Method A) Rt 4.47 min (Purity: 98.8%).

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. washThe organic layer was washed with water (3×), brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-cca1b6e32a7e41da972872b3a6cb1733
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

関連ノート

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