Chloromethyl Methyl Ether → 4-Bromo-2-methoxy-3-(methoxymethoxy)phenol

HRID 2171120Notes

Reaction equation

HRID 2171120 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][CH2:20]Cl>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[C:3]=1[O:11][CH2:18][O:19][CH3:20]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 674653914-Bromo-2-methoxybenzene-1,3-diol

Product 1

HCID 674654874-Bromo-2-methoxy-3-(methoxymethoxy)phenolYield 43.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirring solution of 4-bromo-2-methoxybenzene-1,3-diol (4.5 g, 20.54 mmol) in acetone (40 mL) at 0° C. was added potassium carbonate (2.83 g, 20.54 mmol) and methoxymethyl chloride (1.32 g, 17.39 mmol). The resultant reaction mixture was stirred at RT for 7 h. The reaction mixture was quenched with ice-cold water, the solid was filtered and the filtrate was concentrated under reduced pressure to leave a residue having the crude product. The crude product was purified by column chromatography (silica gel, 0-10% ethyl acetate in pet ether) to afford 4-Bromo-2-methoxy-3-(methoxymethoxy)phenol as a liquid (2 g, 37%).

Workup

  1. customThe resultant reaction mixture
  2. customThe reaction mixture was quenched with ice-cold water
  3. filtrationthe solid was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto leave a residue
  6. customThe crude product was purified by column chromatography (silica gel, 0-10% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-70c5848311664a1c9d2768cf5c83a726
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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