Chlorotrimethylsilane → Methyl 2-(4-(bromomethyl)phenyl)acetate

HRID 43347

Reaction equation

HRID 43347 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]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 45190564-(Bromomethyl)phenylacetic acid

Product 1

HCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was twice re-dissolved in MeOH (200 ml)
  3. concentrationre-concentrated

Sources & evidence

ORD record
ord-b6f12120b68f4cc6a572fb91af9e6f91
Source dataset
uspto-grants-2013_09
Patent number
US08536182B2

Linked notes

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