p-Toluenesulfonic acid → HCID 21938505, compound

HRID 1453247Notes

Reaction equation

HRID 1453247 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([Cl:11])[CH:3]=1.[CH2:12]([O:14]C(OCC)OCC)[CH3:13].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C(O)CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:9])[O:14][CH2:12][CH2:13][O:10]2)=[C:4]([Cl:11])[CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 155609501-(4-Bromo-2-chlorophenyl)ethan-1-one

Product 1

HCID 21938505HCID 21938505, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

1-(4-Bromo-2-chloro-phenyl)-ethanone (from step 2 below) (1.86 g, 5.66 mmol), below was dissolved in ethylene glycol (5 mL). Triethylorthoformate (0.71 g, 4.79 mmol), and tosic acid (0.02 g) were added and reaction was stirred under nitrogen for 24 hours at room temperature. The resulting reaction mixture was poured into NaHCO3 (10 mL) and extracted with EtOAC. The combined organics were washed with water (10 mL) and brine (10 mL) then dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (5% EtOAc in Hexanes) to yield the intermediate ether as a colorless oil (0.69 g, 58%). 1H NMR (CDCl3): δ 1.77 (s, 3H), 3.74-3.79 (m, 2H), 4.04-4.09 (m, 2H), 7.37 (dd, J=8.5, 1.9 Hz, 1H), 7.52 (d, J=8.5 Hz, 1H), 7.55 (d, J=1.9 Hz, 1H). ESIMS (MH+): 278.2.

Workup

  1. customreaction
  2. customThe resulting reaction mixture
  3. extractionextracted with EtOAC
  4. washThe combined organics were washed with water (10 mL) and brine (10 mL)
  5. dry with materialthen dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash chromatography (5% EtOAc in Hexanes)
  9. customto yield the intermediate ether as a colorless oil (0.69 g, 58%)

Sources & evidence

ORD record
ord-3931ad003a6f499fbeeffa7a69a27c12
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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