Methyl iodide → Methyl 4-chloro-3'-methylbiphenyl-3-carboxylate

HRID 404952Notes

Reaction equation

HRID 404952 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)=[CH:4][C:3]=1[C:15]([OH:17])=[O:16].[C:18]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)=[CH:4][C:3]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 509948242-Chloro-5-(3-methylphenyl)benzoic acid

Product 1

HCID 66799518Methyl 4-chloro-3'-methylbiphenyl-3-carboxylateYield 98.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-chloro-3′-methylbiphenyl-3-carboxylic acid (1.70 g, 6.90 mmol), K2CO3 (7.0 g, 50.6 mmol) and CH3I (3 mL, 48 mmol) in acetone (30 mL) was heated under reflux for 1 h. After filtration and evaporation of excess CH3I, the residue was washed with water and extracted with ethyl acetate, dried over anhydrous Na2SO4, and evaporated solvent in vacuo to provide crude methyl 4-chloro-3′-methylbiphenyl-3-carboxylate (1.77 g, 98%) as a brown oil. 1H NMR (300 MHz, DMSO-d6): δ 8.04 (s, 1H), 7.85 (d, J=7.8 Hz, 1H), 7.64 (d, J=8.1 Hz, 1H), 7.52-7.47 (m, 2H), 7.38 (t, J=7.8 Hz, 1H), 7.23 (d, J=7.5 Hz, 1H), 3.90 (s, 3H), 2.39 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. filtrationAfter filtration and evaporation of excess CH3I
  4. washthe residue was washed with water
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated solvent in vacuo

Sources & evidence

ORD record
ord-caf11283fb0144be95768567a829f0d0
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

Loading…