Chloromethyl Methyl Ether → HCID 67466846, compound

HRID 2171183Notes

Reaction equation

HRID 2171183 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([OH: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[C:3]([O:11][CH2:18][O:19][CH3:20])=[C:4]([OH:10])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 37058743-Bromo-6-methoxybenzene-1,2-diol

Product 1

HCID 67466846HCID 67466846, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirring solution of 3-bromo-6-methoxybenzene-1,2-diol (500 mg, 2.27 mmol) in acetone (40 mL) at 0° C. was added potassium carbonate (313 mg, 2.27 mmol) and methoxymethyl chloride (183 mg, 2.27 mmol) and the resultant reaction mixture was stirred at RT for 2 h. The reaction mixture was filtered and filtrate was concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, 0-8% ethyl acetate in pet ether) afforded 3-Bromo-6-methoxy-2-(methoxymethoxy)phenol as a liquid (230 mg, 38%).

Workup

  1. customthe resultant reaction mixture
  2. filtrationThe reaction mixture was filtered
  3. concentrationfiltrate was concentrated under reduced pressure
  4. customPurification of the residue by column chromatography (silica gel, 0-8% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-6fd061c1189b47b99dca461e0df65b93
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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