Water → 2-Iodo-1-(methyloxy)-3-[(2-methyl-2-propen-1-yl)oxy]benzene

HRID 527541Notes

Reaction equation

HRID 527541 reaction equation
[I:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:10].[H-].[Na+].Cl[CH2:14][C:15]([CH3:17])=[CH2:16].O>CN(C=O)C>[I:1][C:2]1[C:3]([O:10][CH2:16][C:15]([CH3:17])=[CH2:14])=[CH:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 141047372-Iodo-3-methoxyphenol2×

Product 1

HCID 679668282-Iodo-1-(methyloxy)-3-[(2-methyl-2-propen-1-yl)oxy]benzeneYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-iodo-3-(methyloxy)phenol (Intermediate 47, 10.3 g) in DMF (100 ml, SCRC) was added NaH (60%, wt., 1.977 g, 49.4 mmol) portionwise. The reaction mixture was stirred at room temperature for 1 hour and 3-chloro-2-methyl-1-propene (3.73 g, 41.2 mmol, Aldrich) was added. The resulting mixture was stirred at room temperature for 2 hours and water (50 ml) was added. The reaction mixture was extracted with ethyl acetate (3 times 200 ml, SCRC) and the combined organic layer were dried, evaporated and purified by silica gel chromatography with as eluents EtOAc/PE (1/30) to afford the title compound as a yellow liquid (11.6 g)

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 hours
  2. extractionThe reaction mixture was extracted with ethyl acetate (3 times 200 ml, SCRC)
  3. customthe combined organic layer were dried
  4. customevaporated
  5. custompurified by silica gel chromatography with as eluents EtOAc/PE (1/30)

Sources & evidence

ORD record
ord-ab30e689126149ff89890cca70b0cd18
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…