Hydrochloric Acid → HCID 57671757, compound

HRID 1511512Notes

Reaction equation

HRID 1511512 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[I-:10].[Na+].CC1C=CC(S(NCl)(=O)=O)=CC=1.Cl>CN(C=O)C.O>[I:10][C:8]1[CH:7]=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 90073-MethoxyphenolHCID 31388Tosylchloramide

Product 1

HCID 57671757HCID 57671757, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Methoxyphenol (2.0 ml, 18.2 mmol) was dissolved in dry DMF (50 ml). Sodium iodide (3.3 g, 21.9 mmol) and chloramine-T (5.0 g, 21.9 mmol) was added to the mixture and the reaction was stirred at room temperature for one hour. The reaction mixture was diluted with water (150 ml), acidified with 5% hydrochloric acid solution and extracted with ethyl acetate (2×100 ml). The organic layer was washed with 5% sodium thiosulphate solution (200 ml) and dried over sodium sulphate. The product was purified by flash chromatography on silica gel twice (first with dichloromethane, then with 20% ethyl acetate in petroleum ether). The yield was 0.82 g (18%). 1H NMR (CDCl3, 500 MHz): δ 7.52 (1H, d, J=8.5 Hz), 6.63 (1H, d, J=3.0 Hz), 6.37 (1H, dd, J=8.5 Hz, 3.0 Hz), 5.27 (1H, s), 3.81 (3H, s).

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. washThe organic layer was washed with 5% sodium thiosulphate solution (200 ml)
  3. dry with materialdried over sodium sulphate
  4. customThe product was purified by flash chromatography on silica gel twice (first with dichloromethane

Sources & evidence

ORD record
ord-6d1c61be25d4491085935f287a1a29f0
Source dataset
uspto-grants-2012_07
Patent number
US08216856B2

Reaction notes

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