Methyl iodide → 2-(3-Bromo-4-methoxy-phenyl)-propionic acid ethyl ester

HRID 563595Notes

Reaction equation

HRID 563595 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([Br:14])[CH:7]=1)[CH3:2].IC.[CH3:18][Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([Br:14])[CH:7]=1)[CH3:18])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 57419861Ethyl 3-bromo-4-methoxyphenylacetate

Product 1

HCID 574588042-(3-Bromo-4-methoxy-phenyl)-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To (3-bromo-4-methoxy-phenyl)-acetic acid ethyl ester (12.2 mmol) in THF was added iodomethane (0.75 mL, 12.2 mmol), and the mixture was cooled to −78° C. Sodium bis(trimethylsilyl)amide (1 M in THF; 12.2 mL, 12.2 mmol) was added, and subsequent work-up gave the title compound.

Sources & evidence

ORD record
ord-45b065c0adc14736b6c446ea9622ce3a
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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