Water → 2-(2-Bromo-3-methylphenyl)ethylmethylether

HRID 1369595Notes

Reaction equation

HRID 1369595 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][OH:11].[H-].[Na+].[CH3:14]I.O>O1CCCC1.C(O)(=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 226725712-(2-Bromo-3-methylphenyl)ethan-1-ol

Product 1

HCID 226726222-(2-Bromo-3-methylphenyl)ethylmethyletherYield 89%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(2-bromo-3-methylphenyl)ethanol (1.6 g, 7.4 mmol) in tetrahydrofuran (20 ml) was added sodium hydride (50% in oil) (0.46 g, 9.6 mmol). After stirring the mixture for 15 min methyl iodide (1.6 g, 11.3 mmol) was added and the reaction mixture was stirred for 3 h. at room temperature. Water (0.2 g) was added and then acetic acid (0.2 g). The solvents were evaporated under reduced pressure and purification of the residue by column chromatography on silica gel using methylene chloride as eluent gave 1.5 g (89%) of the desired product as an oil.

Workup

  1. additionwas added
  2. customThe solvents were evaporated under reduced pressure and purification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-500588af3ac24c489f0de1166e92e73f
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

Loading…