Methyl iodide → 4-Benzyloxy-2-methoxy-1-methylsulfanyl-benzene

HRID 748892Notes

Reaction equation

HRID 748892 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([SH:16])=[C:13](O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O-:20])([O-])=O.[K+].[K+].[CH3:23]I>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([S:16][CH3:23])=[C:13]([O:20][CH3:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 219047055-(Benzyloxy)-2-sulfanylphenol

Product 1

HCID 219046734-Benzyloxy-2-methoxy-1-methylsulfanyl-benzeneYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 5-benzyloxy-2-mercapto-phenol (17.8 g, 76.72 mmol) in DMF (300 mL) and add K2CO3 (31.8 g, 0.23 mol) and MeI (32.7 g, 0.23 mol). Stir the reaction mixture at room temperature overnight. Add water (800 mL) and extract the aqueous layer with EtOAc (3×800 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica, 5-20% of EtOAc/hexane) to give 13.5 g of 4-benzyloxy-2-methoxy-1-methylsulfanyl-benzene (68%).

Workup

  1. extractionAdd water (800 mL) and extract the aqueous layer with EtOAc (3×800 mL)
  2. dry with materialCombine the organic layers and dry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify by flash column chromatography (silica, 5-20% of EtOAc/hexane)

Sources & evidence

ORD record
ord-bdf46cc23c1b4e2ab826951cab3bd5b9
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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