Sodium Chloride → 4-Fluoro-3-(methoxymethyl)aniline

HRID 880131Notes

Reaction equation

HRID 880131 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([F:12])=[C:8]([CH2:10][OH:11])[CH:9]=1.[CH3:13]I.[Cl-].[Na+]>C(OCC)C.O1CCCC1>[F:12][C:7]1[CH:6]=[CH:5][C:4]([NH2:3])=[CH:9][C:8]=1[CH2:10][O:11][CH3:13]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2737680(5-Amino-2-fluorophenyl)methanol

Product 1

HCID 668813234-Fluoro-3-(methoxymethyl)aniline

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a round-bottomed flask, 374 mg of sodium hydride at 60% are introduced into 10 ml of tetrahydrofuran, 1g of (5-amino-2-fluorophenyl)methanol and 0.441 ml of methyl iodide. After stirring at ambient temperature for one hour, a solution of sodium chloride and diethyl ether are added. The organic phase is extracted and then washed with water until pH=7. It is then dried over magnesium sulphate, filtered, and concentrated under reduced pressure. 900 mg of 4-fluoro-3-(methoxymethyl)aniline are obtained in the form of a black oil, which is used as it is in the next stage.

Workup

  1. extractionThe organic phase is extracted
  2. washwashed with water until pH=7
  3. dry with materialIt is then dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07d15adbaa7d44d18f736a522fe5d4d3
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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