Hydrochloric Acid → HCID 58158634, compound

HRID 2095755Notes

Reaction equation

HRID 2095755 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.C(=O)([O-])O.[Na+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].Cl>O1CCCC1.O>[F:9][C:4]1[CH:3]=[C:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 2735918Phenol, 4-amino-2-fluoro-

Product 1

HCID 58158634HCID 58158634, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a suspension of 4-amino-2-fluorophenol (60 g, 472 mmol) in tetrahydrofuran/water (=1/1, 600 mL) was added sodium hydrogen carbonate (43.6 g, 519 mmol), and benzyl chloroformate (74.1 mL, 519 mmol) was added dropwise at 0° C. The mixture was stirred at room temperature for 16 hr, 2N hydrochloric acid (150 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, the residue was washed with hexane/diethyl ether (=1/1) and collected by filtration to give the title compound (82.5 g, 67%). The solvent of the filtrate was evaporated under reduced pressure, and the residue was washed with hexane/diethyl ether (=1/1) and collected by filtration to give the title compound (17.7 g, 14%).

Workup

  1. additionwas added dropwise at 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. washthe residue was washed with hexane/diethyl ether (=1/1)
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-66c71a5f1019478294c5949e35e39f76
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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