Ammonium Chloride → (6-Fluoro-3-iodo-2-methylphenyl)methanol

HRID 1948670Notes

Reaction equation

HRID 1948670 reaction equation
[F:1][C:2]1[C:7]([C:8](OC)=[O:9])=[C:6]([CH3:12])[C:5]([I:13])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+].[H][H]>C(OCC)C>[F:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([CH3:12])[C:5]([I:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 25517Ammonium Chloride2×HCID 21226445Aluminium lithium hydrideHCID 59450535Methyl 6-fluoro-3-iodo-2-methylbenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 59450541(6-Fluoro-3-iodo-2-methylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of the product from Step B (5.5 g, 18.7 mmol) in diethyl ether (20 ml) was carefully added lithium aluminum hydride (0.8 g, 18.7 mmol). The mixture was stirred at room temperature for 16 h. Saturated aqueous ammonium chloride solution was added dropwise until no hydrogen gas was being generated. A few more drops of saturated aqueous ammonium chloride solution were added and the mixture was stirred at room temperature for 30 min and filtered. The filtrated was dried over magnesium sulfate and concentrated to dryness to give the title compound as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. filtrationfiltered
  3. dry with materialThe filtrated was dried over magnesium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1fd73c74585946c8ba71ff1a9c74a445
Source dataset
uspto-grants-2013_03
Patent number
US08399507B2

Reaction notes

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