N-bromobutanimide → 2-(1-Bromo-ethyl)-4-fluoro-benzonitrile

HRID 1406274ノート

反応式

HRID 1406274 の反応式
[CH2:1]([C:3]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6])[CH3:2].[Br:12]N1C(=O)CCC1=O>FC(C1C=CC=CC=1)(F)F.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:12][CH:1]([C:3]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6])[CH3:2]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 234392762-Ethyl-4-fluorobenzonitrile

生成物 1

HCID 682096782-(1-Bromo-ethyl)-4-fluoro-benzonitrile収率 93.5%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 7368(Trifluoromethyl)benzene溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-ethyl-4-fluoro-benzonitrile (prepared according to WO 07039178, page 116) (1.14 g, 7.6 mmol) in trifluoromethyl-benzene (30 mL) was added N-bromosuccinimide (1.63 g, 9.1 mmol, 1.2 eq.) followed by azobisisobutyronitrile (0.025 g, 0.15 mmol, 0.02 eq.). The mixture was heated to 100° C. for 18 hr under an atmosphere of nitrogen and then cooled to room temperature. The mixture was filtered and filtrate partitioned with aqueous sodium sulphite solution (1M, 20 mL). The organic phase was washed with water (20 mL) and then evaporated under reduced pressure to give the title compound as a beige solid (1.62 g, 93%).

後処理

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered
  3. customfiltrate partitioned with aqueous sodium sulphite solution (1M, 20 mL)
  4. washThe organic phase was washed with water (20 mL)
  5. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-cfb20df412604c48a216f192cf4672dc
出典データセット
uspto-grants-2014_12
特許番号
US08916593B2

反応ノート

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