Ethylene Glycol → HCID 22735928、化合物

HRID 51062ノート

反応式

HRID 51062 の反応式
[CH2:1]([OH:4])[CH2:2][OH:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[C:24](=O)[CH3:25].C([O-])(O)=O.[Na+]>C1C=CC=CC=1.O>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[C:24]1([CH3:25])[O:4][CH2:1][CH2:2][O:3]1

参加物

7

反応物 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 227360801-(2-Bromo-5-fluorophenyl)ethan-1-one

生成物 1

HCID 22735928HCID 22735928、化合物収率 60.2%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

Ethylene glycol (25.6 mL, 458 mmol) and p-toluenesulfonic acid (4.36 g, 22.9 g) were added to a solution of 1-(2-bromo-5-fluorophenyl)ethanone (10.5 g, 45.8 mmol) stirring in benzene (250 mL). The reaction mixture was equipped with a Dean Stark trap containing 4.0 angstrom molecular sieves and refluxed for 16 h. The reaction was transferred to a separatory funnel containing a 1:1 mixture of H2O and sat. NaHCO3 (aq) and extracted with EtOAc (3×100 mL). The combined organics were washed with H2O, brine, dried over Na2SO4 and concentrated. The resulting oil was purified by column chromatography to give 2-(2-bromo-5-fluorophenyl)-2-methyl-1,3-dioxolane (7.20 g) in 58% yield. 1H NMR (CDCl3, 300 MHz) δ2.60 (s, 3 H) 4.02-4.20 (m, 4H), 6.85-6.90 (m, 1H), 7.29-7.33 (m, 1H), 7.48-7.56 (m, 1H).

後処理

  1. customThe reaction mixture was equipped with a Dean Stark trap
  2. additioncontaining 4.0 angstrom molecular sieves
  3. temperaturerefluxed for 16 h
  4. customThe reaction was transferred to a separatory funnel
  5. additioncontaining
  6. extractionextracted with EtOAc (3×100 mL)
  7. washThe combined organics were washed with H2O, brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe resulting oil was purified by column chromatography

出典と根拠

ORDレコード
ord-53ddd933fc464c58bafcb5d535a76f82
出典データセット
uspto-grants-2004_03
特許番号
US06713471B1

反応ノート

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