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

HRID 429946Notes

Reaction equation

HRID 429946 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=1[OH:16].C(N(C(C)C)CC)(C)C.[CH3:26][O:27][CH2:28]Cl>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C(Cl)Cl>[CH3:26][O:27][CH2:28][O:16][C:3]1[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][C:6]([C:8]([CH3:9])([CH3:10])[CH3:11])=[CH:7][C:2]=1[Br:1]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 5198222-Bromo-4,6-di-tert-butylphenol2×

Product 1

HCID 225926381-Bromo-3,5-bis(1,1-dimethylethyl)-2-(methoxymethoxy)benzeneYield 95.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2-bromo-4,6-di-t-butylphenol (Compound D 2.54 g, 8.88 mmol) and catalytic amount of Bu4NI in 20 ml of dry CH2Cl2 at 0° C. was added diisopropylethylamine (9.51 ml, 53 mmol), followed by methoxymethyl chloride (2.02 ml, 26.6 mmol). The reaction mixture was heated to 45° C. for 12 hours. The reaction mixture was then washed with 10% citric acid, then NaHCO3 (sat.), brine, and dried over MgSO4. After filtration and removal of the solvent under reduced pressure, the residue was purified by column chromatography (pure hexane) to yield the title compound (2.79 g) as a colorless oil.

Workup

  1. washThe reaction mixture was then washed with 10% citric acid
  2. dry with materialNaHCO3 (sat.), brine, and dried over MgSO4
  3. filtrationAfter filtration and removal of the solvent under reduced pressure
  4. customthe residue was purified by column chromatography (pure hexane)

Sources & evidence

ORD record
ord-df490391df204e4eb0c5092b8d5f315e
Source dataset
uspto-grants-2001_11
Patent number
US06320047B1

Reaction notes

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