Chlorotrimethylsilane → Methyl 2-fluorophenylacetate

HRID 1689444Notes

Reaction equation

HRID 1689444 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[CH3:12][Si](Cl)(C)C>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 67979Benzeneacetic acid, 2-fluoro-

Product 1

HCID 2733230Methyl 2-fluorophenylacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(2-fluorophenyl)acetic acid (9.6 g) in methanol (200 mL) was treated with trimethylsilyl chloride (10 mL) and the mixture heated at reflux for 2 hours. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution, the organic layer was dried over sodium sulphate, filtered and the solvent removed under reduced pressure to afford the subtitled compound. Yield 9.7 g.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  5. dry with materialthe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-9d27412937b44673a12356c3e38f628d
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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