Sodium Iodide → HCID 59191346, compound

HRID 1023901Notes

Reaction equation

HRID 1023901 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[CH:14][C:13]=2[OH:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[CH:14][C:13]=2[O:21][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 59191264HCID 59191264, compound

Product 1

HCID 59191346HCID 59191346, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-hydroxy-4-propylphenyl 4-methylbenzenesulfonate (0.11 mmol; 33 mg) under argon, in acetone (0.2 mL), were added K2CO3 (0.13 mmol; 18 mg), NaI (0.02 mmol; 3 mg), and benzylbromide (0.12 mmol; 0.015 mL). The reaction was stirred at 40° C. for 5 hr. The reaction mixture was then hydrolysed with NH4Cl sat. (3 mL) and extracted with ethyl acetate (3*5 mL). Combined organic phases were washed with saturated NaHCO3 (3 mL), dried over MgSO4, concentrated. The residue was purified by preparative TLC (dichlorométhane) to yield the title compound as a clear oil (28 mg; 0.07 mmol; 64%).

Workup

  1. extractionhydrolysed with NH4Cl sat. (3 mL) and extracted with ethyl acetate (3*5 mL)
  2. washCombined organic phases were washed with saturated NaHCO3 (3 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC (dichlorométhane)

Sources & evidence

ORD record
ord-a95164b6f3b244f69663d96b6cd9026f
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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