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

HRID 1739360노트

반응식

HRID 1739360 반응식
[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

참가 물질

5

반응물 3

HCID 702EthanolHCID 8471TriethylamineHCID 707414-Bromobenzaldehyde

생성물 1

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

시약·촉매·용매 1

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide촉매

실험 절차

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), δ7.52 (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.

후처리

  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

출처 및 근거

ORD 기록
ord-7cf0864fef8e4d3999f77b965635226a
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05965679

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