Trimethylsilyldiazomethane → Benzeneacetic acid, 2-(bromomethyl)-, methyl ester

HRID 1866927Notes

Reaction equation

HRID 1866927 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11].[CH3:13][Si](C=[N+]=[N-])(C)C>C1COCC1>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 12889260[2-(Bromomethyl)phenyl]acetic acid

Product 1

HCID 15168495Benzeneacetic acid, 2-(bromomethyl)-, methyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of (2-bromomethylphenyl)acetic acid (1 g, 4.4 mmol) in THF (2.4 mL) was added trimethylsilyldiazomethane (3 mL of a 2 M solution in hexanes, 6 mmol), and the reaction mixture was stirred for 14 h. The reaction was quenched with AcOH, and the solvent was removed under reduced pressure. Purification by flash column chromatography (silica, eluent 98:2 to 94:6 methylene chloride/hexanes) afforded methyl (2-bromomethylphenyl)acetate as a light yellow solid (0.34 g, 32%): 1H NMR (300 MHz, CDCl3) δ 7.40-7.20 (m, 4H), 4.59 (s, 2H), 3.81 (s 2H), 3.71 (s, 3H).

Workup

  1. customThe reaction was quenched with AcOH
  2. customthe solvent was removed under reduced pressure
  3. customPurification by flash column chromatography (silica, eluent 98:2 to 94:6 methylene chloride/hexanes)

Sources & evidence

ORD record
ord-25ce4c23dd6047b99e4328e5588af330
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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