3-Bromo-4-fluorobenzaldehyde → 2-Bromo-4-ethenyl-1-fluorobenzene

HRID 1825040ノート

反応式

HRID 1825040 の反応式
[Li][CH2:2]CCC.[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[F:15])[CH:10]=O>C1COCC1>[Br:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH2:2])[CH:12]=[CH:13][C:14]=1[F:15]

参加物

4

反応物 2

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 218646502-Bromo-4-ethenyl-1-fluorobenzene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of Ph3PCH3Br (57 g) in THF (240 mL) at 0° C. was dropwise added n-BuLi (1.6 N, 100 mL). The resulting mixture was allowed to warm to room temperature and stirred for 1 h. After recooling to 0° C., a solution of 3-bromo-4-fluoro-benzaldehyde (20.3 g) in THF (20 mL) was added. The resulting mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was quenched with water, concentrated, and extracted with methylene chloride. The combined organic layer was dried over magnesium sulfate, concentrated under vacuum. The crude product was purified by flash chromatography eluting with 10% ethyl acetate in hexanes to give the title compound as an oil (18 g).

後処理

  1. customAfter recooling to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 1 h
  4. customThe reaction mixture was quenched with water
  5. concentrationconcentrated
  6. extractionextracted with methylene chloride
  7. dry with materialThe combined organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe crude product was purified by flash chromatography
  10. washeluting with 10% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-67ae454a948b49f983f42cca25d7ae20
出典データセット
uspto-grants-2006_05
特許番号
US07045551B2

反応ノート

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