Sodium Iodide → HCID 54421864, compound

HRID 259941Notes

Reaction equation

HRID 259941 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[O:14][CH3:15].C(=O)([O-])[OH:17].[Na+].[I-].[Na+]>CS(C)=O>[CH3:15][O:14][C:7]1[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][CH2:3][CH:2]=[O:17]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 538225701-(4-Bromobutyl)-2,4-dimethoxybenzene

Product 1

HCID 54421864HCID 54421864, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1-(4-bromobutyl)-2,4-dimethoxybenzene (11.0 g, 40.2 mmol), sodium hydrogen carbonate (6.75 g, 80.3 mmol) and sodium iodide (9.03 g, 60.2 mmol) in DMSO (80 mL) was stirred at 105 C. for 1.5 h. The reaction mixture was allowed to cool to some extent after which ice water (240 mL) was added. The mixture was extracted with diethyl ether (2×200 mL), washed with brine (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (SiO2, hexane-EtOAc, 80:20) yielding the title compound as a colorless liquid (3.56 g): 1H NMR (CDCl3 -d) 9.74 (t, J=1.8 Hz, 1H), 7.00 (d, J=7.9 Hz, 1H), 6.45-6.40 (m, 2H), 3.79 (s, 3H), 3.79 (s, 3H), 2.59 (t, J=7.4 Hz, 2H), 2.44-2.39 (m, 2H), 1.90 (quintet, J=7.4 Hz, 2H); 13C NMR (CDCl3 -d) 202.91, 159.32, 158.28, 130.14, 121.90, 103.78, 98.44, 55.28, 55.16, 43.25, 28.80, 22.50; MS (EI, 70 eV): m/z (rel. int.) 208 (M+, 31), 164 (44), 151 (100), 121 (76), 91 (16).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with diethyl ether (2×200 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (SiO2, hexane-EtOAc, 80:20)

Sources & evidence

ORD record
ord-8e5818109d574411a05f417cac747ea1
Source dataset
uspto-grants-1996_06
Patent number
US05523475

Reaction notes

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