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

HRID 1474395Notes

Reaction equation

HRID 1474395 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:14]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CCOC(C)=O.O>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1

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-fd16f6d6d6aa49649910aed9d0c7800a
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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