Methyl iodide → Ethyl 2-(4-bromophenyl)propanoate
Reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)[CH3:2].[CH3:14][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC>C1COCC1>[CH2:1]([O:3][C:4](=[O:13])[CH:5]([C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)[CH3:14])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
(4-Bromo-phenyl)-acetic acid ethyl ester (6 g, 24.7 mmol) was dissolved in THF (60 mL) and cooled to −78° C. Lithium bis(trimethylsilyl)amide (1 M in THF, 32.11 mL, 32.11 mmol) was added and the reaction stirred at −78° C. for 1 hour. Iodomethane (2.0 mL, 32.11 mmol) in THF (8 mL) was added and the reaction was allowed to warm to room temperature. The reaction was submitted to standard aqueous workup then purified via silica gel chromatography (0-10% EtOAc in hexanes) to afford the title compound.
Workup
- temperatureto warm to room temperature
- customthen purified via silica gel chromatography (0-10% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-46533c2e7a8f44c195e66a470d4eb8a1
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090573B2
Reaction notes
Loading…