3-Fluorophenol → HCID 14575305, compound

HRID 1085678Notes

Reaction equation

HRID 1085678 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[OH-].[Na+]>O>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 97433-FluorophenolHCID 123681,6-DibromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 14575305HCID 14575305, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred mixture of 32.1 parts of 3-fluorophenol, 122 parts of 1,6-dibromohexane and 200 parts of water was dropwise added a solution of 20 parts of sodium hydroxide in 100 parts of water at reflux temperature. Upon completion, stirring was continued for 24 hours at reflux. After cooling, the product was extracted three times with trichloromethane. The combined extracts were dried, filtered and evaporated. The residue was distilled, yielding 40 parts (50%) of 1-[(6-bromohexyl)oxy]-3-fluorobenzene; bp. 45°-90° C. at 0.05 mm pressure (107).

Workup

  1. temperatureat reflux temperature
  2. temperatureat reflux
  3. temperatureAfter cooling
  4. extractionthe product was extracted three times with trichloromethane
  5. customThe combined extracts were dried
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-31f07e0b63644ec8b0631ebc584f4c6b
Source dataset
uspto-grants-1991_04
Patent number
US05010198

Reaction notes

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