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

HRID 240288ノート

反応式

HRID 240288 の反応式
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[Cl:10].[Na+].[I-].[C:13]([S-:15])#[N:14].[K+]>CN(C=O)C.O>[Cl:10][C:4]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:3]=1[CH2:2][N:14]=[C:13]=[S:15]

参加物

6

反応物 3

HCID 5238Sodium IodideHCID 516872Potassium thiocyanateHCID 27736232-Chloro-5-fluorobenzyl bromide

生成物 1

HCID 866548531-Chloro-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
90 °C

実験手順

To a solution of 2-(bromomethyl)-1-chloro-4-fluorobenzene (25, 22.3 g, 100 mmol) in dry DMF (150 mL) were added NaI (16.0 g, 107 mmol) and KSCN (19.5 g, 200 mmol) The mixture was heated under N2 at 90° C. for 18 h. After cooling to RT, the mixture was diluted with water (200 mL), and extracted with EtOAc (200 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-chloro-4-fluoro-2-(isothiocyanatomethyl)benzene (26).

後処理

  1. temperatureAfter cooling to RT
  2. extractionextracted with EtOAc (200 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-9f11df4a5af54f37bed26d2d29688d72
出典データセット
uspto-grants-2014_02
特許番号
US08648073B2

反応ノート

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