Potassium Carbonate → HCID 67465591, compound

HRID 2171184Notes

Reaction equation

HRID 2171184 reaction equation
[Br:1][C:2]1[C:3]([O:11][CH2:12][O:13][CH3:14])=[C:4]([OH:10])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH:21]1([CH2:24]Br)[CH2:23][CH2:22]1>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:24][CH:21]2[CH2:23][CH2:22]2)[C:3]=1[O:11][CH2:12][O:13][CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 67466846HCID 67466846, compound

Product 1

HCID 67465591HCID 67465591, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirring solution of 3-bromo-6-methoxy-2-(methoxymethoxy)phenol (12 g, 0.045 mol) in acetonitrile (100 mL) at 0° C. was added potassium carbonate (18 g, 0.135 mol) and cyclopropylmethyl bromide (9 g, 0.067 mol) and the resultant reaction mixture was stirred for 1 h at RT. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 0-12% ethyl acetate in pet ether) to afford 1-Bromo-3-(cyclopropylmethoxy)-4-methoxy-2-(methoxymethoxy)benzene as a solid (5.5 g, 38%).

Workup

  1. customthe resultant reaction mixture
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel, 0-12% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-c5257943ab174d788140b7b57606f356
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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