Thiophosgene → 5-Fluoro-4-isothiocyanato-2-(trifluoromethyl)benzonitrile

HRID 1504946ノート

反応式

HRID 1504946 の反応式
[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[C:15](Cl)(Cl)=[S:16]>C1COCC1.O>[F:10][C:9]1[C:2]([N:1]=[C:15]=[S:16])=[CH:3][C:4]([C:11]([F:14])([F:12])[F:13])=[C:5]([CH:8]=1)[C:6]#[N:7]

参加物

5

反応物 2

HCID 10040ThiophosgeneHCID 682929284-Amino-5-fluoro-2-(trifluoromethyl)benzonitrile

生成物 1

HCID 867118105-Fluoro-4-isothiocyanato-2-(trifluoromethyl)benzonitrile収率 88%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of the compound 25 (660 mg, 3.25 mmol) in THF (6 mL) was added a solution of thiophosgene (1 mL, 13 mmol) in water (1 mL) slowly at room temperature. The reaction mixture was stirred for 1 h, then concentrated in vacuo. The residue was diluted with H2O. The aqueous solution was extracted with ethyl acetate. The organic layers were combined and washed with aq.NaHCO3 and brine, dried over Na2SO4, filtered and concentrated to provide the title compound 3d (700 mg, 88%) as a light yellow solid, which was used directly in next step without further purification. 1H NMR (400 MHz, CDCl3) δ7.63 (d, 1H, J=8.5 Hz), 7.57 (d, 1H, J=6.9 Hz).

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with H2O
  3. extractionThe aqueous solution was extracted with ethyl acetate
  4. washwashed with aq
  5. dry with materialNaHCO3 and brine, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-b503dfbe286947bc9b160b8fa3abac6f
出典データセット
uspto-grants-2015_12
特許番号
US09216957B2

反応ノート

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