Methanol → Methyl 2-chloro-4-cyano-5-methoxybenzoate

HRID 219877Notes

Reaction equation

HRID 219877 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O=S(Cl)Cl.[CH3:19]O>>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 675283752-Chloro-4-cyano-5-methoxybenzoic acid

Product 1

HCID 67529853Methyl 2-chloro-4-cyano-5-methoxybenzoateYield 90%

Conditions

Temperature
0 °C

Procedure

2-chloro-4-cyano-5-methoxybenzoic acid (600 mg; 2.84 mmol; 1 eq.) was dissolved in MeOH (12 mL). The solution was cooled down to 0° C. SOCl2 (0.62 mL; 8.51 mmol; 3 eq.) was added dropwise. The reaction mixture was stirred at RT for 24 hours. The reaction mixture was concentrated and the residue was taken up in EtOAc. The organic layer was washed with a saturated aqueous solution of NaHCO3, then brine, dried over MgSO4, concentrated affording the title compound as a yellow solid (0.58 g, 90%). 1H NMR (DMSO-d6, 300 MHz) δ 8.09 (s, 1H), 7.57 (s, 1H), 3.96 (s, 3H), 3.89 (s, 3H). HPLC (Method A) Rt 4.08 min (Purity: 94.3%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washThe organic layer was washed with a saturated aqueous solution of NaHCO3
  3. dry with materialbrine, dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fb7ef2110c8548f4ba99a6cb41253729
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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