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

HRID 1699431Notes

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

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 (100%) of the expected compound are collected in the form of an orange oil.

Workup

customThe solution obtained
stirringthe reaction mixture is stirred for one hour at room temperature
extractionextracted with ethyl ether
customthe organic phase is separated
dry with materialdried over magnesium sulphate
customevaporated
custom46.00 g (100%) of the expected compound are collected in the form of an orange oil

Sources & evidence

ORD record: ord-14946a640b6e484aa929213934992a4d
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06346546B1

Reaction notes

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