Benzyl chloroformate → HCID 58158451, compound

HRID 2095761Notes

Reaction equation

HRID 2095761 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].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]>O1CCCC1.O>[F:9][C:3]1[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=1[NH:1][C:16](=[O:17])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 27359194-Amino-3-fluorophenol

Product 1

HCID 58158451HCID 58158451, compoundYield 920.4%

Reagents, catalysts & solvents 1

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

Procedure

To a suspension of 4-amino-3-fluorophenol (50 g, 39.3 mmol) in tetrahydrofuran/water (=1/1, 500 mL) was added sodium hydrogen carbonate (36.3 g, 39.3 mmol), and benzyl chloroformate (62 mL, 43.3 mmol) was added dropwise at room temperature. The mixture was stirred at room temperature for 16 hr, and extracted with ethyl acetate (1000 mL). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent 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 (94.5 g, 92%).

Workup

  1. additionwas added dropwise at room temperature
  2. extractionextracted with ethyl acetate (1000 mL)
  3. washThe organic layer was washed with saturated brine
  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-006dda6be81f4be48b78181156f632c3
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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