4-Fluorophenol → HCID 20392581, compound

HRID 1863314Notes

Reaction equation

HRID 1863314 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C[O-].[Na+].Br[CH:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)[C:14]([O:16][CH3:17])=[O:15]>CO>[CH3:17][O:16][C:14](=[O:15])[CH:13]([C:18]1[CH:19]=[CH:20][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:22][CH:23]=1)[O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 20392581HCID 20392581, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.87 g of p-fluorophenol in 50 ml of methanol is added 1.07 g of sodium methoxide. To this solution is added 5.4 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate and the mixture is refluxed for 18 hours. The mixture is concentrated to 1/2 volume and poured into 150 ml of ice and water. The mixture is extracted with ether and the cold extracts washed with 50 ml of 2 N NaOH and with saline. After drying (MgSO4), the extracts are concentrated under vacuum to give the product as an amber colored oil.

Workup

  1. temperaturethe mixture is refluxed for 18 hours
  2. concentrationThe mixture is concentrated to 1/2 volume
  3. additionpoured into 150 ml of ice and water
  4. extractionThe mixture is extracted with ether
  5. washthe cold extracts washed with 50 ml of 2 N NaOH and with saline
  6. dry with materialAfter drying (MgSO4)
  7. concentrationthe extracts are concentrated under vacuum

Sources & evidence

ORD record
ord-b98f4a7bb19b4c8fb4d3724b8839003f
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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