Ethyl Acetate → (2-Bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol

HRID 1175295ノート

反応式

HRID 1175295 の反応式
[Br:1][C:2]1[CH:11]=[C:10]([C:12](=O)[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:9]([Cl:22])=[CH:8][C:3]=1[C:4](OC)=[O:5].C([SiH](CC)CC)C.FC(F)(F)S(O)(=O)=O.CCOC(C)=O>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:9]([Cl:22])=[CH:8][C:3]=1[CH2:4][OH:5]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 59557708HCID 59557708、化合物

生成物 1

HCID 59467877(2-Bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

To a solution of methyl 2-bromo-5-chloro-4-(4-ethylbenzoyl)benzoate (7.64 g, 20 mmol) in 2,2,2-trifluoroacetic acid (38 mL) was added triethylsilane (5.88 mL, 40 mmol) under argon. After it was stirred for 10 min at room temperature, trifluoromethanesulfonic acid (0.1 mL) was added. The reaction temperature was raised from 26° C. to reflux. After stirring for 2 h, TLC (PE:EtOAc=6:1, Rf=0.7) showed the reaction was complete. The reaction mixture was evaporated and the residue was dissolved in EtOAc (150 mL). The organic layer was washed 2× with H2O, 2× with NaHCO3, and 2× with brine, and then dried over anhydrous Na2SO4 Concentration under reduced pressure provided the title compound as a white solid. Yield: 7.2 g (100%). 1H-NMR (CDCl3, 300 MHz) δ 7.85 (s, 1H), 7.44 (s, 1H), 7.17 (s, 1H), 7.14 (s, 1H), 7.10 (s, 1H), 7.07 (s, 1H), 4.05 (s, 2H), 3.92 (s, 3H), 2.63 (q, J=7.8 Hz, 2H), 1.24 (t, J=7.8 Hz, 3H).

後処理

  1. temperatureThe reaction temperature was raised from 26° C.
  2. temperatureto reflux
  3. stirringAfter stirring for 2 h
  4. customThe reaction mixture was evaporated
  5. dissolutionthe residue was dissolved in EtOAc (150 mL)
  6. washThe organic layer was washed 2× with H2O, 2× with NaHCO3, and 2× with brine
  7. dry with materialdried over anhydrous Na2SO4 Concentration under reduced pressure

出典と根拠

ORDレコード
ord-146e5230de2e41f682d188903bae214f
出典データセット
uspto-grants-2010_11
特許番号
US07838498B2

反応ノート

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