Hydrochloric Acid → HCID 59192512, compound

HRID 2384012Notes

Reaction equation

HRID 2384012 reaction equation
Cl.O.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[C:6]([OH:17])[C:5]=1[F:18]>[Zn].C1(C)C=CC=CC=1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[C:6]([OH:17])[C:5]=1[F:18]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid3×HCID 962Water2×HCID 59192517HCID 59192517, compound

Product 1

HCID 59192512HCID 59192512, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Procedure

A mixture of zinc pieces (11.4 g), mercuric chloride (3.0 g), concentrated hydrochloric acid (4.6 mL) and water (140 mL) was stirred at room temperature for 5 minutes. The solvent was then decanted off. To the solid, were added concentrated hydrochloric acid (41 mL), water (18.6 mL), toluene (23 mL) and 4-(4-chloro-3-fluoro-2-hydroxy-phenyl)-4-oxo-butyric acid (8.6 g, 35 mmol). The resulting mixture was heated at reflux for 2 days, with the addition of concentrated hydrochloric acid in 12 hour intervals. The reaction mixture was cooled and extracted with ether (50 mL×3). The collected organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give pure 4-(4-chloro-3-fluoro-2-hydroxy-phenyl)-butyric acid (6.0 g, 74%), which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.74 (dt, 2H), 2.20 (t, J=7.40 Hz, 2H), 2.57 (t, J=7.56 Hz, 2H), 6.87-6.92 (m, 2H), 9.90 (br s, 1H), 12.03 (br s, 1H).

Workup

  1. customThe solvent was then decanted off
  2. temperatureThe resulting mixture was heated
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ether (50 mL×3)
  5. dry with materialThe collected organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c18d8daeac649cda249adde4bebf2de
Source dataset
uspto-grants-2012_09
Patent number
US08263656B2

Reaction notes

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