3-Fluorophenol → HCID 14575305, compound

HRID 1723428Notes

Reaction equation

HRID 1723428 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-b0e06f2a0c51497c9949c037c2036954
Source dataset
uspto-grants-1989_08
Patent number
US04861785

Reaction notes

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