Lithium iodide → HCID 66801516、化合物

HRID 2366309ノート

反応式

HRID 2366309 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([I:12])[CH:9]=[C:8]([F:13])[C:3]=1[C:4]([O:6]C)=[O:5].[Li+].[I-]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]([I:12])[CH:9]=[C:8]([F:13])[C:3]=1[C:4]([OH:6])=[O:5]

参加物

4

反応物 2

HCID 66321Lithium iodideHCID 66801721Benzoic acid, 2-chloro-6-fluoro-4-iodo-, methyl ester

生成物 1

HCID 66801516HCID 66801516、化合物収率 111.8%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
115 °C

実験手順

To a solution of methyl 2-chloro-6-fluoro-4-iodo-benzoate (4.48 g, 14.2 mmol) in pyridine (28 mL) was added LiI (4.0 g, 29.9 mmol). The reaction mixture was heated at 115° C. for 4 hours. The solvent was removed under vacuum. The resultant solid was dissolved in water, and extracted with EtOAc. The aqueous layer was acidified with 1 N HCl to pH=4, extracted with EtOAc (3×30 mL). The combined organic phases were washed with 10% citric acid (2×30 mL), brine, dried (Na2SO4), filtered and concentrated to give the title compound (4.77 g, quantitative yield) as a yellow solid. 1H NMR (400 MHz, methanol-d4) δ 7.73 (s, 1H), 7.62 (dd, J=8.4, 1.1 Hz, 1H). LCMS (ESI) m/z 300.8 [M+H+].

後処理

  1. customThe solvent was removed under vacuum
  2. dissolutionThe resultant solid was dissolved in water
  3. extractionextracted with EtOAc
  4. extractionextracted with EtOAc (3×30 mL)
  5. washThe combined organic phases were washed with 10% citric acid (2×30 mL), brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-41f883e4295341098283d7c7e6f12cfe
出典データセット
uspto-grants-2014_04
特許番号
US08697708B2

反応ノート

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