Iodoethane → 1-Bromo-4-ethoxy-3-methoxy-2-(methoxymethoxy)benzene

HRID 2171121Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirring solution of 4-bromo-2-methoxy-3-(methoxymethoxy)phenol (600 mg, 2.28 mmol) in acetonitrile (20 mL) was added potassium carbonate (944 mg, 6.84 mmol) and ethyl iodide (711 mg, 4.56 mmol) and the resultant reaction mixture was heated to 70° C. for 3 h. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, 0-7% ethyl acetate in pet ether) to afford 1-Bromo-4-ethoxy-3-methoxy-2-(methoxymethoxy)benzene as a solid (525 mg, 79%).

Workup

customthe resultant reaction mixture
filtrationThe reaction mixture was filtered through celite
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained residue was purified by column chromatography (silica gel, 0-7% ethyl acetate in pet ether)

Sources & evidence

ORD record: ord-8eac6110f45e47b69437bcc20a42aa7a
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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