Hydrochloric Acid → 4-((Benzyloxy)carbonyl)-2-fluorobenzoic acid

HRID 2233060Notes

Reaction equation

HRID 2233060 reaction equation
[O-]Cl=O.[Na+].[CH2:5]([O:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][C:17]([CH:20]=[O:21])=[C:16]([F:22])[CH:15]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S(=O)(=O)([OH:26])N.Cl>O.CC#N>[CH2:5]([O:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:26])=[O:21])=[C:16]([F:22])[CH:15]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 59295103Benzyl 3-fluoro-4-formylbenzoate

Product 1

HCID 592950924-((Benzyloxy)carbonyl)-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of 80% NaClO2 (0.19 mol) in H2O (100 mL) is added dropwise to a solution of crude 3-fluoro-4-formyl benzoic acid benzyl ester (6, 0.19 mol) and sulfamic acid (0.19 mol) in H2O (300 mL) and CH3CN (150 mL). After stirring for 1 h, the reaction mixture is poured into 1 N HCl and extracted three times with EtOAc. The combined organic layers are washed with brine, dried over MgSO4, and evaporated in vacuo. Crystals are collected by filtration and washed with ether/hexane (1:1) to give 2-fluoroterephthalic acid 4-benzyl ester (7) 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. filtrationCrystals are collected by filtration
  6. washwashed with ether/hexane (1:1)

Sources & evidence

ORD record
ord-f0849a56174342cb8f383ea9749e37ef
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

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