Hydrochloric Acid → 2-Fluoro-4-(methoxycarbonyl)benzoic acid

HRID 2233058Notes

Reaction equation

HRID 2233058 reaction equation
[O-]Cl=O.[Na+].[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[C:10]([F:16])[CH:9]=1.S(=O)(=O)([OH:20])N.[O-]S([O-])=O.[Na+].[Na+].Cl>O.CC#N>[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:20])=[O:15])=[C:10]([F:16])[CH:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5987Sulfamic AcidHCID 24437Sodium SulfiteHCID 18766342Methyl 3-fluoro-4-formylbenzoateHCID 23668197Sodium Chlorite

Product 1

HCID 592950932-Fluoro-4-(methoxycarbonyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of 80% NaClO2 (0.13 mol) in H2O (50 mL) is added dropwise to a solution of crude 3-fluoro-4-formyl benzoic acid methyl ester (4, 0.12 mol) and sulfamic acid (0.13 mol) in H2O (50 mL) and CH3CN (100 mL). After stirring for 1 h, the reaction mixture is poured into saturated Na2SO3 aqueous solution and 1 N HCl, and extracted three times with EtOAc. The combined organic layers are washed with brine, dried over MgSO4, and evaporated in vacuo. The crystals are collected by filtration and washed with ether/hexane (1:1) to give 2-fluoroterephthalic acid 4-methyl ester (5) as white solid.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. filtrationThe crystals are collected by filtration
  6. washwashed with ether/hexane (1:1)

Sources & evidence

ORD record
ord-0c06f1883c3644efb487d13743aeaef3
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

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