Chloromethyl Methyl Ether → 1-Bromo-3,5-bis(1,1-dimethylethyl)-2-(methoxymethoxy)benzene

HRID 22996Notes

Reaction equation

HRID 22996 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([Br:15])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:19][O:20][CH2:21]Cl.Cl.C(OCC)C>CN(C=O)C>[Br:15][C:7]1[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]=1[O:16][CH2:19][O:20][CH3:21]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 5198222-Bromo-4,6-di-tert-butylphenolHCID 10953452Ether hydrochloride

Product 1

HCID 225926381-Bromo-3,5-bis(1,1-dimethylethyl)-2-(methoxymethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
7.5 °C

Procedure

40.00 g (140.2 mmol) of 2,4-di-tert-butyl-6-bromophenol and 400 ml of DMF are introduced into a one liter three-necked flask. The solution obtained is cooled to 5-10° C., 4.70 g of sodium hydride are added and the mixture is stirred at 10° C. for 30 minutes. 11.7 ml (154.0 mmol) of chloromethyl methyl ether are then added dropwise and the reaction mixture is stirred for one hour at room temperature. The reaction mixture is poured into a 1N HCl/ethyl ether mixture and extracted with ethyl ether and the organic phase is separated by settling, dried over magnesium sulphate and evaporated. 46.00 g (130%) of the expected compound are collected in the form of an orange oil.

Workup

  1. customThe solution obtained
  2. stirringthe reaction mixture is stirred for one hour at room temperature
  3. extractionextracted with ethyl ether
  4. customthe organic phase is separated
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. custom46.00 g (130%) of the expected compound are collected in the form of an orange oil

Sources & evidence

ORD record
ord-fb17e6201ae24177862d7baad47c5a19
Source dataset
uspto-grants-2005_02
Patent number
US06849658B2

Reaction notes

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