Methyl iodide → Methyl 2-(3-bromo-2-methoxyphenyl)acetate

HRID 1187138Notes

Reaction equation

HRID 1187138 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[C:6]=1[OH:12].[C:14]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CCOC(C)=O.O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[C:6]=1[O:12][CH3:14]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12159074Methyl 2-(3-bromo-2-hydroxyphenyl)acetate

Product 1

HCID 66643982Methyl 2-(3-bromo-2-methoxyphenyl)acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl(3-bromo-2-hydroxyphenyl)acetate (18.7 g, 76.3 mmol) in 200 mL of DMF was added K2CO3 (52.7 g, 382 mmol), MeI (14.0 mL, 229 mmol). The mixture was stirred at 50° C. for 3 hours. The reaction solution was diluted with EtOAc and water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified column chromatography to give methyl[3-bromo-2-(methyloxy)phenyl]acetate.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated
  3. customThe residue was purified column chromatography

Sources & evidence

ORD record
ord-212cae91328741c19917b3066d404d58
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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