2-Amino-6-fluorobenzoic acid → (2-Amino-6-fluorophenyl)methanol
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturecooled to 0° C. again
- additionNa2SO410H2O (10 g) was added slowly
- stirringwith stirring for 20 minutes
- filtrationThe mixture was filtered
- washthe solid was washed with THF
- 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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