Sodium Iodide → 1-Bromo-4-fluoro-2-(isothiocyanatomethyl)benzene

HRID 240276

反応式

HRID 240276 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9]Br.[Na+].[I-].[C:13]([S-:15])#[N:14].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][N:14]=[C:13]=[S:15]

参加物

6

反応物 3

HCID 5238Sodium IodideHCID 516872Potassium thiocyanateHCID 5179721-Bromo-2-(bromomethyl)-4-fluorobenzene

生成物 1

HCID 866548501-Bromo-4-fluoro-2-(isothiocyanatomethyl)benzene

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 1-bromo-2-(bromomethyl)-4-fluorobenzene (12, 5.36 g, 20.0 mmol) in dry DMF (20 mL) was added NaI (1.20 g, 8.00 mmol) and KSCN (3.88 g, 40.0 mmol). The mixture was heated under N2 at 80° C. for 12 h. After cooling to RT, the mixture was diluted with water (100 mL), and extracted with EtOAc (50 mL×2). The combined extracts were washed with brine, dried over MgSO4 and concentrated to give crude product. This was purified by column chromatography on silica gel, and eluted with petroleum ether to provide 1-bromo-4-fluoro-2-(isothiocyanatomethyl)benzene (13).

後処理

  1. temperatureAfter cooling to RT
  2. extractionextracted with EtOAc (50 mL×2)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customThis was purified by column chromatography on silica gel
  8. washeluted with petroleum ether

出典と根拠

ORDレコード
ord-5dcaa496b0594bcb9620f803335dbacb
出典データセット
uspto-grants-2014_02
特許番号
US08648073B2

関連ノート

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