1-Bromohexane → 4-n-Hexyloxy-2-fluorobromobenzene

HRID 327365Notes

Reaction equation

HRID 327365 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[F:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:2]([O:15][C:12]1[CH:13]=[CH:14][C:9]([Br:8])=[C:10]([F:16])[CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 27791534-Bromo-3-fluorophenol

Product 1

HCID 191078664-n-Hexyloxy-2-fluorobromobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 1-bromohexane (9.33 g) in acetone (20 ml) is added dropwise to a stirred mixture of 4-bromo-3-fluorophenol (9.00 g) and potassium carbonate (13.5 g) in acetone 75 ml) at room temperature. The stirred mixture is heated under reflux for 21 h (i.e. until glc analysis revealed a complete reaction). The product is extracted into ether twice, and the combined ether extracts are washed with water, 10% sodium hydroxide, water and dried (MgSO4). The solvent is removed under vacuo and the residue is distilled (bp 100°-105° C. at 0.1 mm Hg) to yield a colourless liquid.

Workup

  1. temperatureThe stirred mixture is heated
  2. temperatureunder reflux for 21 h (i.e. until glc analysis
  3. customa complete reaction)
  4. extractionThe product is extracted into ether twice
  5. washthe combined ether extracts are washed with water, 10% sodium hydroxide, water
  6. dry with materialdried (MgSO4)
  7. customThe solvent is removed under vacuo
  8. distillationthe residue is distilled (bp 100°-105° C. at 0.1 mm Hg)
  9. customto yield a colourless liquid

Sources & evidence

ORD record
ord-858bbcdcf57d47bd8a71f61f772d3446
Source dataset
uspto-grants-1993_12
Patent number
US05273680

Reaction notes

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