Chloromethyl Methyl Ether → 1-Bromo-3-(methoxymethoxy)-2-methylbenzene

HRID 2307553Notes

Reaction equation

HRID 2307553 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:12][O:13][CH2:14]Cl>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:12][O:13][CH3:14])[C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 111714303-Bromo-2-methylphenol

Product 1

HCID 226068611-Bromo-3-(methoxymethoxy)-2-methylbenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

13.9 g (74 mmol) of 3-bromo-2-methylphenol are dissolved in 120 mL of dimethylformamide and the mixture is cooled to 0° C. 3.6 g (90 mmol) of 60% sodium hydride are then added portionwise and the medium is stirred for 1 hour. 6.8 mL (90 mmol) of methoxymethyl chloride are then added slowly and the medium is warmed to room temperature and then stirred for 1 hour. After the usual treatment, the residue is purified by chromatography on silica gel (eluent: 80 heptane/20 ethyl acetate). The desired product is obtained in the form of a colourless oil (m=16.2 g; Y=95%).

Workup

  1. temperaturethe medium is warmed to room temperature
  2. stirringstirred for 1 hour
  3. customAfter the usual treatment, the residue is purified by chromatography on silica gel (eluent: 80 heptane/20 ethyl acetate)

Sources & evidence

ORD record
ord-f67322277bb34f118ca28191424cf730
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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