3-Bromo-2-chloro-5-nitropyridine → 3-Bromo-2-fluoro-5-nitropyridine

HRID 367105ノート

反応式

HRID 367105 の反応式
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[F-:12].[K+]>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(#N)C>[Br:1][C:2]1[C:3]([F:12])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

参加物

5

反応物 2

HCID 2308893-Bromo-2-chloro-5-nitropyridineHCID 522689Potassium Fluoride

生成物 1

HCID 3451243-Bromo-2-fluoro-5-nitropyridine収率 56.8%

試薬・触媒・溶媒 2

HCID 2724163Tetraphenylphosphonium Bromide触媒HCID 6342Acetonitrile溶媒

実験手順

3-Bromo-2-chloro-5-nitropyridine (119 g, 0.500 mol, prepared according to V. Koch and S. Schnatterer, Synthesis, 1990, 497-498), potassium fluoride (79.5 g, 1.37 mol), and tetraphenylphosphonium bromide (109 g, 0.260 mol) were combined in acetonitrile (1.5 L) and heated at reflux for 4 days until GLC indicated complete consumption of the 3-bromo-2-chloro-5-nitropyridine. The volume of the mixture was reduced to 750 mL in vacuo then and diluted with 2 L of ether. The mixture was filtered and the filtrate concentrated. The residue was triturated with hot hexane (2×1 L then 2×0.5 L) and the combined hexane extracts were concentrated to give 62.8 g (54%) of the title compound: 1H NMR (DMSO-d6 300 MHz) δ 9.14 (m, 2H).

後処理

  1. temperatureheated
  2. temperatureat reflux for 4 days until GLC
  3. customconsumption of the 3-bromo-2-chloro-5-nitropyridine
  4. additiondiluted with 2 L of ether
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated
  7. customThe residue was triturated with hot hexane (2×1 L
  8. concentration2×0.5 L) and the combined hexane extracts were concentrated

出典と根拠

ORDレコード
ord-a91fad9e5a2c48ebba221ac3dcf4518e
出典データセット
uspto-grants-2000_10
特許番号
US06133253

反応ノート

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