Ethylene Glycol → 2-(5-Bromo-2-fluorophenyl)-1,3-dioxolane

HRID 1271914ノート

反応式

HRID 1271914 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].O.CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25].C1(C)C=CC=CC=1>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:7]2[O:25][CH2:24][CH2:23][O:8]2)[CH:9]=1

参加物

6

反応物 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 7363275-Bromo-2-fluorobenzaldehyde

生成物 1

HCID 184555852-(5-Bromo-2-fluorophenyl)-1,3-dioxolane

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

5-Bromo-2-fluorobenzaldehyde (14.6 mL, 0.123 mol, Avocado) is combined with 4-methylbenzenesulfonic acid hydrate (2.34 g, 12.0 mmol, Aldrich), ethylene glycol (13.7 mL, 0.25 mol, Mallinkrodt) and toluene (75 mL). The mixture is heated to reflux overnight. The resulting solution is diluted into EtOAc (100 mL) and washed 2× with saturated NaHCO3, 1× with water and 1× with brine (170 mL ea). The organic layer is dried over Na2SO4 and filtered. The solvent is removed by rotary evaporation and the product is purified on a Biotage Flash 75L (800 g silica) cartridge using 96:3:1 heptane:EtOAc:TEA as eluent.

後処理

  1. temperatureThe mixture is heated
  2. temperatureto reflux overnight
  3. washwashed 2× with saturated NaHCO3, 1× with water and 1× with brine (170 mL ea)
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent is removed by rotary evaporation
  7. customthe product is purified on a Biotage Flash 75L (800 g silica) cartridge

出典と根拠

ORDレコード
ord-6d00bbb6730c42659ee94c1be1203e50
出典データセット
uspto-grants-2007_04
特許番号
US07208490B2

反応ノート

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