Sodium Sulfate → (2-Amino-6-fluorophenyl)methanol

HRID 448918Notes

Reaction equation

HRID 448918 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:9]=1[C:10](O)=[O:11].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 5211422-Amino-6-fluorobenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11521092(2-Amino-6-fluorophenyl)methanolYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LAH (987 mg, 26 mmol) was added slowly to a solution of 2-amino-6-fluoro-benzoic acid (2.69 g, 17.3 mmol) in dry THF (20 mL) at 0° C. The mixture was stirred at room temperature for approximately 1 hr and cooled to 0° C. again. Na2SO4. 10H2O (10 g) was added slowly with stirring for 20 minutes. The mixture was filtered, the solid was washed with THF. The solution was concentrated to yield a yellow solid as (2-amino-6-fluoro-phenyl)-methanol (2.49 g). MS [M−OH]+: 124.1; tR=0.57 min. (method 1)

Workup

  1. temperaturecooled to 0° C. again
  2. addition10H2O (10 g) was added slowly
  3. stirringwith stirring for 20 minutes
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with THF
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-1ebad88f8c4f4acdaf6118055c1e51ed
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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