Methyl chloroformate → 4-Fluoro-2-methylphenyl Methoxyformate

HRID 1691810Notes

Reaction equation

HRID 1691810 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[H-].[Na+].Cl[C:13]([O:15][CH3:16])=[O:14]>C1COCC1>[CH3:16][O:15][C:13](=[O:14])[O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[CH3:9]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 1362954-Fluoro-2-methylphenol

Product 1

HCID 106790444-Fluoro-2-methylphenyl MethoxyformateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Following the procedure of J. Med. Chem. 1999, 42, 5369, 4-fluoro-2-methylphenol (10.0 g, 79.0 mmol) was dissolved in THF and the mixture was cooled to 0° C. NaH (1 eq, 3.16 g of a 60% dispersion in oil) was added carefully. After gas evolution ceased, methyl chloroformate (1 eq, 6.8 ml) was added. The mixture was allowed to warm to room temperature and stir for 3 hours. The mixture was washed with cold water, dried over anhydrous sodium sulfate, filtered and then concentrated in vacuo to give carbonic acid 4-fluoro-2-methyl-phenyl ester methyl ester (12.8 g, 88.0%) as an oil.

Workup

  1. temperatureto warm to room temperature
  2. washThe mixture was washed with cold water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cae88ee387f46279dcf05269a6b95a4
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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