Methanol → HCID 67529335, compound

HRID 219868Notes

Reaction equation

HRID 219868 reaction equation
[C:1]([C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([F:14])[CH:4]=1)#[N:2].O=S(Cl)Cl.[CH3:19]O>>[C:1]([C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:6]([C:7]([O:9][CH3:19])=[O:8])=[C:5]([F:14])[CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 67528967HCID 67528967, compound

Product 1

HCID 67529335HCID 67529335, compoundYield 80%

Conditions

Temperature
0 °C

Procedure

4-Cyano-2-fluoro-5-methoxybenzoic acid (75 mg; 0.38 mmol; 1 eq.) was dissolved in MeOH (1 mL). The solution was cooled down to 0° C. SOCl2 (0.11 mL; 1.54 mmol; 4 eq.) was added dropwise. After addition, the reaction mixture was stirred at RT overnight. As the reaction was complete, solvents were evaporated. The crude mixture was dissolved in EtOAc and washed with NaHCO3 sat and brine. The organic phase was dried over MgSO4, filtrated and evaporated, affording the title product as an orange solid (64 mg; 80%). HPLC (Method A) Rt 3.68 min (Purity: 94.5%).

Workup

  1. additionAfter addition
  2. customsolvents were evaporated
  3. dissolutionThe crude mixture was dissolved in EtOAc
  4. washwashed with NaHCO3
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltrated
  7. customevaporated

Sources & evidence

ORD record
ord-cb4b67bf92c4459996cc1620c0652c34
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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