Trifluoroacetic acid → 6-Bromo-2-o-tolyl-chroman

HRID 59767ノート

反応式

HRID 59767 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:6][CH:5]2O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:6][CH2:5]2

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 71293089HCID 71293089、化合物

生成物 1

HCID 712928256-Bromo-2-o-tolyl-chroman

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 6-bromo-2-o-tolyl-chroman-4-ol (11.9 g, 37.3 mmol) in dichloromethane (130 ml) at 0° C. triethylsilane (29.6 g, 255 mmol, 6.8 eq) and trifluoroacetic acid (75 ml, 27 eq) were added. The solution was stirred at room temperature for 2.5 h. The solvent was removed under reduced pressure and the residue separated between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic layers washed with water and saturated aqueous solution of sodium hydrogencarbonate, dried with sodium sulfate and filtered, and the solvent removed under reduced pressure. The crude product was purified by column chromatography (silica gel; ethyl acetate/heptane gradient). 6-Bromo-2-o-tolyl-chroman was obtained as a pale yellow oil (7.10 g, 63%).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue separated between water and ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers washed with water and saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customThe crude product was purified by column chromatography (silica gel; ethyl acetate/heptane gradient)

出典と根拠

ORDレコード
ord-3139fa5e46c040158902953e33b69ac5
出典データセット
uspto-grants-2016_09
特許番号
US09440941B2

反応ノート

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