Water → (2-Amino-6-fluorophenyl)methanol

HRID 1294564Notes

Reaction equation

HRID 1294564 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:9]=1[C:10](OC)=[O:11].O>C(OCC)C>[NH2:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 2818492Methyl 2-amino-6-fluorobenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11521092(2-Amino-6-fluorophenyl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

676.3 mg (17.8 mmol) lithium aluminium hydride are placed in 65 ml diethyl ether under an N2 atmosphere and cooled to 0° C. 2.01 g (11.9 mmol) methyl 2-amino-6-fluoro-benzoate, dissolved in 65 ml diethyl ether, are slowly added dropwise thereto and the mixture is stirred for 2 h at 0° C. Then the reaction mixture is combined dropwise at 0° C. with 100 ml dist. H2O. The aqueous phase is extracted twice with 100 ml diethyl ether. The combined organic phases are washed once with 100 ml of a saturated, aqueous NaCl solution, dried with MgSO4 and the solvent is eliminated in vacuo.

Workup

  1. additionare slowly added dropwise
  2. customis combined dropwise at 0° C. with 100 ml dist
  3. extractionThe aqueous phase is extracted twice with 100 ml diethyl ether
  4. washThe combined organic phases are washed once with 100 ml of a saturated, aqueous NaCl solution
  5. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-3eb4e8fb77de4557863d99f18e7016a8
Source dataset
uspto-grants-2007_07
Patent number
US07241769B2

Reaction notes

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