Chlorotrimethylsilane → Methyl 2-(4-(bromomethyl)phenyl)acetate
Reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[CH3:13][Si](Cl)(C)C>CO>[Br:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(bromomethyl)phenylacetic acid (20 g, 87.3 mmol) in MeOH (200 ml) was added trimethylsilylchloride (2 ml) and the reaction stirred for 2 h. The solvent was removed in vacuo and the residue was twice re-dissolved in MeOH (200 ml) and re-concentrated to give the title compound (21.08 g). δH (CDCl3, 250 MHz) 7.36 (2H, d), 7.26 (2H, d), 4.49 (2H, s), 3.69 (3H, s), 3.62 (2H, s).
Workup
- customThe solvent was removed in vacuo
- dissolutionthe residue was twice re-dissolved in MeOH (200 ml)
- concentrationre-concentrated
Sources & evidence
- ORD record
- ord-b6f12120b68f4cc6a572fb91af9e6f91
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536182B2
Reaction notes
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