2-Amino-6-fluorobenzoic acid → (2-Amino-6-fluorophenyl)methanol

HRID 661671Notes

Reaction equation

HRID 661671 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]>C1COCC1>[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:9]=1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 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. Na2SO410H2O (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. additionNa2SO410H2O (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-4f609a07dcf1441d944124fc40e5b4fd
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

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