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

HRID 1271914노트

반응식

HRID 1271914 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6d00bbb6730c42659ee94c1be1203e50
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208490B2

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