Chlorotrimethylsilane → Methyl 2-Chloro-4-fluorobenzoate

HRID 601021Notes

Reaction equation

HRID 601021 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[Si](C)(C)[CH3:14]>CO>[CH3:14][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 752592-Chloro-4-fluorobenzoic acid

Product 1

HCID 2763551Methyl 2-Chloro-4-fluorobenzoateYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-chloro-4-fluorobenzoic acid (6.5 g, 37 mmol) in methanol (100 mL) was treated with chlorotrimethylsilane (14.0 mL, 111 mmol), stirred 24 h at room temperature and evaporated. The residue was dissolved in dichloromethane, washed with sodium bicarbonate, dried (sodium sulfate) and evaporated to provide 2-chloro-4-fluoro-benzoic acid methyl ester (7.01 g, 99% yield) as a pale yellow oil. 1H-NMR (CDCl3, 500 MHz) 7.93 (m, 1H), 7.22 (m, 1H), 7.06 (m, 1H), 3.95 (s, 3H) ppm; MS (FIA) 189.1 (M+H); HPLC (Method A) 3.37 min.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with sodium bicarbonate
  4. dry with materialdried (sodium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-3fb7c2ff1389450dbc6ce3d71752089c
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

Loading…