Methanol → Methyl 2-fluoro-5-hydroxybenzoate

HRID 714117Notes

Reaction equation

HRID 714117 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>>[F:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27744802-Fluoro-5-hydroxybenzoic acid

Product 1

HCID 46311141Methyl 2-fluoro-5-hydroxybenzoate

Procedure

The obtained 2-fluoro-5-hydroxybenzoic acid (3e) (780 mg, 5 mmol) was dissolved in 100 mL methanol. Thionyl chloride (0.8 mL, 10 mmol) was added dropwise under the condition of ice bath (0° C.) and stirring, and then refluxed for two hours. The reaction solution was concentrated, and then column chromatography (petroleum ether:ethyl acetate=2:1) was performed to isolate methyl 2-fluoro-5-hydroxybenzoate (3f), 833 mg white solid (yield 98%). 1H NMR (600 MHz, DMSO-d6) δ 9.73 (s, 1H), 7.20-7.18 (m, 1H), 7.13-7.09 (m, 1H), 6.99-6.97 (m, 1H), 3.80 (s, 3H); ESI-MS m/z: calculated for 170.04. found 171.25 [M+H]+.

Workup

  1. temperaturerefluxed for two hours
  2. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-92f514314a264178881809374e2fed4e
Source dataset
uspto-grants-2015_11
Patent number
US09187430B2

Reaction notes

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