Hydrochloric Acid → HCID 22078400, compound

HRID 1428384Notes

Reaction equation

HRID 1428384 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].Cl[C:11]([O:13][CH3:14])=[O:12].Cl>ClCCl>[F:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([OH:9])[C:2]=1[NH:1][C:11](=[O:12])[O:13][CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 27827782-amino-3-fluorophenol

Product 1

HCID 22078400HCID 22078400, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-amino-3-fluorophenol (2.07 g) and dichloromethane (100 mL) were added TEA (2.29 mL) and methyl chloroformate (1.27 mL) under ice-cooling, followed by stirring at room temperature for 3 hours. The reaction mixture was ice-cooled, and 0.5 M hydrochloric acid solution was added thereto, followed by stirring for 10 minutes. Then, the organic layer was separated. The organic layer was washed with brine, dried over Na2SO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=100/0-75/25) to obtain methyl (2-fluoro-6-hydroxyphenyl)carbamate (2.55 g).

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. stirringby stirring for 10 minutes
  4. customThen, the organic layer was separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=100/0-75/25)

Sources & evidence

ORD record
ord-1787a579f2fd4bd8a97b9a8e3b2956a7
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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