Ethylene Glycol → HCID 11129071, compound

HRID 2105082Notes

Reaction equation

HRID 2105082 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:12](O)[CH2:13][OH:14]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2([CH3:10])[O:14][CH2:13][CH2:12][O:11]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 705081-(3-Bromo-4-fluorophenyl)ethan-1-one

Product 1

HCID 11129071HCID 11129071, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(3-bromo-4-fluorophenyl)ethanone (7.5 g, 34.5 mmol), ethylene glycol (10 mL) and a catalytic amount of tosyl acid was refluxed in toluene (100 mL) for 18 h with a Dean-Stark trap. The crude reaction mixture was quenched with H2O (100 mL) extracted with EtOAc (3×50 mL), washed organic layer with H2O, brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient) to afford 8.8 g of Intermediate 416.1. 1H NMR (400 MHz, CDCl3) δ ppm 1.61 (s, 3H) 3.69-3.81 (m, 2H) 3.97-4.09 (m, 2H) 7.07 (t, J=8.35 Hz, 1H) 7.32-7.43 (m, 1H) 7.67 (dd, J=6.59, 2.20 Hz, 1H).

Workup

  1. customThe crude reaction mixture
  2. customwas quenched with H2O (100 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. washwashed organic layer with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-4facc3c46fe6493091dd696b360f3c82
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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