4-Fluorophenol → HCID 15096975, compound

HRID 345559Notes

Reaction equation

HRID 345559 reaction equation
[O-]CC.[Na+].[Na].[F:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.Br[CH2:15][CH:16]([CH3:19])[CH2:17][Cl:18]>C(O)C>[Cl:18][CH2:17][CH:16]([CH3:19])[CH2:15][O:13][C:10]1[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 97324-FluorophenolHCID 955661-Bromo-3-chloro-2-methylpropaneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 15096975HCID 15096975, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred sodium ethoxide solution, prepared starting from 3.5 parts of sodium in 24 parts of ethanol, were added 16.8 parts of 4-fluorophenol. After stirring for 15 minutes, there was added dropwise a solution of 77 parts of 1-bromo-3-chloro-2-methylpropane in 72 parts of ethanol at room temperature. Upon completion, stirring was continued for 20 hours at reflux temperature. The reaction mixture was filtered and the filtrate was evaporated. The residue was taken up in 2,2'-oxybispropane. The organic phase was washed with water and with alkaline water 5%, dried, filtered and evaporated. The residue was distilled, yielding 11.6 parts of 1-(3-chloro-2-methylpropoxy)-4-fluorobenzene; bp. 126° C. (water-jet) (intermediate 82).

Workup

  1. stirringUpon completion, stirring
  2. waitwas continued for 20 hours
  3. temperatureat reflux temperature
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate was evaporated
  6. washThe organic phase was washed with water and with alkaline water 5%
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe residue was distilled

Sources & evidence

ORD record
ord-4195b27e207e41ffb9e7105d91940b57
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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