Triethylamine → 4-Chloro-2-trifluoromethyl-8-vinyl-quinoline

HRID 505855ノート

反応式

HRID 505855 の反応式
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:8]=[C:7]2[Cl:16].[CH2:17](N(CC)CC)[CH3:18]>C(O)C>[Cl:16][C:7]1[C:6]2[C:11](=[C:2]([CH:17]=[CH2:18])[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:8]=1

参加物

4

反応物 2

HCID 8471TriethylamineHCID 6283708-Bromo-4-chloro-2-(trifluoromethyl)quinoline

生成物 1

HCID 670395294-Chloro-2-trifluoromethyl-8-vinyl-quinoline収率 72.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A suspension of 2.00 g (6.25 mmol) 8-bromo-4-chloro-2-trifluoromethylquinoline (commercially available from Maybridge, Cornwall, UK), 258 mg (0.31 mmol) PdCl2dppf CH2Cl2, 1.29 g (9.37 mmol) potassium vinyl tetrafluoroborate and 0.88 ml (6.28 mmol) triethylamine in 40 ml ethanol was heated at reflux for 3 h. The resulting yellow suspension was filtered and the filtrate evaporated to dryness. The residue was suspended in ethyl acetate, filtered and the filtrate extracted with water. The organic layer was evaporated to dryness and the isolated crude product purified by silica gel chromatography (hexane) to yield 1.17 g (72%) of the title compound as white crystals. MS: 257.1 (M+). 1H-NMR (300 MHz, CDCl3): 5.58 (dd, J=11.1, 1.1 Hz, 1H); 6.07 (dd, J=17.8, 1.1 Hz, 1H); 7.75 (t, J=7.7 Hz, 1H); 7.81 (s, 1H); 7.99 (dd, J=17.8, 1.1 Hz, 1H); 8.09 (d, J=7.2 Hz, 1H); 8.23 (d, J=8.4 Hz, 1H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. filtrationThe resulting yellow suspension was filtered
  4. customthe filtrate evaporated to dryness
  5. filtrationfiltered
  6. extractionthe filtrate extracted with water
  7. customThe organic layer was evaporated to dryness
  8. customthe isolated crude product
  9. custompurified by silica gel chromatography (hexane)

出典と根拠

ORDレコード
ord-86e36a0f4eef4d159998f27b60910f0b
出典データセット
uspto-grants-2010_08
特許番号
US07781586B2

反応ノート

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