Ethanol → 1,2-Bis(4-bromophenyl)-2-hydroxyethanone

HRID 1595952ノート

反応式

HRID 1595952 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(N([CH2:15][CH3:16])CC)C.[CH2:17]([OH:19])[CH3:18]>[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([CH:17]([C:18]2[CH:16]=[CH:15][C:2]([Br:1])=[CH:3][CH:4]=2)[OH:19])=[O:7])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 702EthanolHCID 8471TriethylamineHCID 707414-Bromobenzaldehyde

生成物 1

HCID 39382431,2-Bis(4-bromophenyl)-2-hydroxyethanone収率 100%

試薬・触媒・溶媒 1

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide触媒

実験手順

A solution of 4-bromobenzaldehyde (25.0 g, 0.135 mol), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (1.70 g, 0.0068 mol) and triethylamine (4.10 g, 0.0405 mol) in ethanol (125 mL) is stirred at room temperature for 60 hours. The reaction mixture is concentrated to dryness, then taken up in CH2Cl2 (150 mL), washed with 1 M HCl and saturated aqueous NaHCO3 and dried (Na2SO4), then concentrated, giving 25.2 g (100 percent) of a viscous yellow oil which solidifies upon standing at room temperature. 1H NMR (CDCl3) δ 7.73 (d, J=8.5 Hz, 2H), δ 7.52 (d, J=8.5 Hz, 2H), 7.44 (d, J=8.2 Hz, 2H), 7.17 (d, J=8.2 Hz, 2H) 13C NMR (CDCl3) δ 197.33, 137.56, 132.33, 132.13, 131.90, 130.43, 129.46, 129.31, 122.93, 75.68.

後処理

  1. concentrationThe reaction mixture is concentrated to dryness
  2. washwashed with 1 M HCl and saturated aqueous NaHCO3
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-85965dbd71ed4b318b4d8901b5404da1
出典データセット
uspto-grants-2001_09
特許番号
US06288188B1

反応ノート

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