1,3-Dibromopropane → HCID 21443206, compound

HRID 328630Notes

Reaction equation

HRID 328630 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[OH:11])[CH:2]=[CH2:3].[Br:12][CH2:13][CH2:14][CH2:15]Br.[OH-].[Na+]>O>[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:15][CH2:14][CH2:13][Br:12])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 113441122-Allyl-4-fluorophenol

Product 1

HCID 21443206HCID 21443206, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred and refluxing mixture of 162 parts of 2-allyl-4-fluorophenol, 363 parts of 1,3-dibromopropane in 700 parts of water is added dropwise a solution of 56 parts of sodium hydroxide in 175 parts of water. Upon completion, the whole is stirred and refluxed for 8 hours. After cooling, the aqueous layer is separated and extracted with chloroform. The extract is dried over magnesium sulfate, filtered and evaporated. The oily residue is distilled twice, yielding 142 parts of 3-allyl-4-(3-bromopropoxy)fluorobenzene; bp. 160° -170° C. at 14 mm. pressure.

Workup

  1. temperaturerefluxing
  2. stirringUpon completion, the whole is stirred
  3. temperaturerefluxed for 8 hours
  4. temperatureAfter cooling
  5. customthe aqueous layer is separated
  6. extractionextracted with chloroform
  7. dry with materialThe extract is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe oily residue is distilled twice

Sources & evidence

ORD record
ord-87b3195e6c63404d8f64072d7ea9afb9
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Reaction notes

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