Hydrochloric Acid → 5-Chloro-2-(4-fluorophenoxy)benzoic acid

HRID 1293219Notes

Reaction equation

HRID 1293219 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].O1CCCC1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57572285HCID 57572285, compound

Product 1

HCID 457924105-Chloro-2-(4-fluorophenoxy)benzoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 5-chloro-2-(4-fluorophenoxy)benzoate (step 1, 2.60 g, 9.26 mmol), tetrahydrofuran (20 mL), methanol (20 mL), and 2 N sodium hydroxide (20 mL) was stirred at room temperature for 3 h. The mixture was poured into 2 N hydrochloric acid (50 mL) and the aqueous mixture was extracted with ethyl acetate (200 mL). The organic layer was dried over magnesium sulfate and evaporated to give 2.41 g (98%) of the title compound as white solids: 1H-NMR (CDCl3) δ 8.11 (1H, d, J=2.8 Hz), 7.43 (1H, dd, J=9.0, 2.8 Hz), 7.14–7.02 (4H, m), 6.80 (1H, d, J=8.8 Hz); MS (ESI) m/z 265 (M−H)−.

Workup

  1. extractionthe aqueous mixture was extracted with ethyl acetate (200 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-073eb9266a3d4a9b8fefc45a0714981f
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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