2-Fluorophenol → HCID 13563908, compound

HRID 1248830Notes

Reaction equation

HRID 1248830 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Br:9][CH2:10]/[CH:11]=[CH:12]/[CH2:13]Br.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:13]/[CH:12]=[CH:11]/[CH2:10][Br:9]

Participants

5

Reactant 3

HCID 97072-FluorophenolHCID 11430Potassium CarbonateHCID 641245trans-1,4-Dibromo-2-butene

Product 1

HCID 13563908HCID 13563908, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

100 g (0.9 mole) of 2-fluorophenol and 477 g (2.7 moles) of trans-1,4-dibromobut-2-ene were stirred under reflux with 70 g of K2CO3 in 500 ml of acetone for 5 hours. The mixture was filtered, and acetone was evaporated off under reduced pressure, the residue was taken up in methylene chloride, the solution was washed four times with aqueous 1 N NaOH solution, and the methylene chloride phase was dried with sodium sulfate and freed from unreacted 1,4-dibromobutene under reduced pressure. 175 g of trans-1-(2-fluorophenoxy)-4-bromobut-2-ene remained.

Workup

  1. filtrationThe mixture was filtered
  2. customacetone was evaporated off under reduced pressure
  3. washthe solution was washed four times with aqueous 1 N NaOH solution
  4. dry with materialthe methylene chloride phase was dried with sodium sulfate

Sources & evidence

ORD record
ord-d3d128b5c20948b8b43e7371c8a86311
Source dataset
uspto-grants-1986_12
Patent number
US04626544

Reaction notes

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