Methyl chloroformate → 2-Chloro-4-fluoro-methoxycarbonyloxybenzene

HRID 1164746Notes

Reaction equation

HRID 1164746 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[OH-].[Na+].Cl[C:13]([O:15][CH3:16])=[O:14]>O>[C:13](=[O:14])([O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Cl:1])[O:15][CH3:16]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 748142-Chloro-4-fluorophenol

Product 1

HCID 104884382-Chloro-4-fluoro-methoxycarbonyloxybenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 20.0 g (0.14 mole) of 2-chloro-4-fluorophenol and 6.64 g (0.17 mole) of sodium hydroxide in 100 mL of water at 15° C. was added 17.7 g (0.19 mole) of methyl chloroformate. After complete addition, the mixture was stirred for 15 minutes then extracted with ethyl acetate. The organic phase was washed with a 1N sodium hydroxide solution, then dried over anhydrous magnesium sulfate. The dried extract was filtered, and the filtrate evaporated under reduced pressure to provide methyl (2-chloro-4-fluorophenyl) carbonate as a solid.

Workup

  1. additionAfter complete addition
  2. extractionthen extracted with ethyl acetate
  3. washThe organic phase was washed with a 1N sodium hydroxide solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. extractionThe dried extract
  6. filtrationwas filtered
  7. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-1259ba50f82d47d99279d69f323d0770
Source dataset
uspto-grants-1990_03
Patent number
US04906286

Reaction notes

Loading…