Reaction #160126

Reaction equation

2-fluoro-4-hydroxy-benzoic acid

thionyl chloride

methanol

→

methyl 2-fluoro-4-hydroxy-benzoate

Yield 40.0%

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated in vacuo
2. 2
   workup.ADDITIONdiluted with DCM (100 mL)
3. 3
   Washwashed with aqueous saturated NaHCO3 (2×50 mL) solution
4. 4
   OtherThe organics were separated
5. 5
   Dryingdried with MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo

Procedure

To a solution of 2-fluoro-4-hydroxy-benzoic acid (5.32 g, 34.1 mmol) in methanol (21 mL) was added thionyl chloride (4.86 g, 3 mL, 40.9 mmol) dropwise and the reaction mixture was stirred at 40° C. for 3 hours. The reaction mixture was concentrated in vacuo and diluted with DCM (100 mL) and washed with aqueous saturated NaHCO3 (2×50 mL) solution. The organics were separated and dried with MgSO4, filtered and concentrated in vacuo to give methyl 2-fluoro-4-hydroxy-benzoate (2.3 g, 40%). ESI-MS m/z calc. 170.1. Found 171.3 (M+1)+; Retention time: 0.84 minutes (3 min run).

Source