Chlorotrimethylsilane → Methyl 2-fluorophenylacetate

HRID 471214Notes

Reaction equation

HRID 471214 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-c320173705dc408bbb45dc4b9f4ffa26
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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