Butyl bromide → 1-Butoxy-2,3-Difluorobenzene

HRID 1511483Notes

Reaction equation

HRID 1511483 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[OH-].[Na+].Br[CH2:13][CH2:14][CH2:15][CH3:16]>O.CCCCCCC>[CH2:13]([O:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[F:1])[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 14798Sodium HydroxideHCID 808792,3-Difluorophenol

Product 1

HCID 27829391-Butoxy-2,3-DifluorobenzeneYield 79.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8900HeptaneSolvent

Conditions

Temperature
30 °C

Procedure

2,3-Difluorophenol (21) (100.0 g) and sodium hydroxide (NaOH; 36.9 g) were added to water (300 ml) under a nitrogen atmosphere, and the stirring was continued at 70° C. 1-Bromobutane (158.0 g) was added thereto, and the stirring was continued at 70° C. for 2 hours. The reaction mixture obtained was cooled to 30° C., heptane (100 ml) and water (100 ml) were added, and mixed. The mixture was then allowed to separate into organic and aqueous phases. The extraction into an organic phase was carried out. The organic phase obtained was washed with brine and dried over anhydrous magnesium sulfate. Then, fractional distillation was carried out under reduced pressure, giving 114.4 g of 4-butoxy-2,3-difluorobenzene (22). The compound (22) obtained was a colorless oil having a boiling point of 109° C. to 110° C./20 mmHg. The yield based on the compound (21) was 80.0%.

Workup

  1. customwas continued at 70° C
  2. customThe reaction mixture obtained
  3. additionmixed
  4. customto separate into organic and aqueous phases
  5. extractionThe extraction into an organic phase
  6. customThe organic phase obtained
  7. washwas washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThen, fractional distillation

Sources & evidence

ORD record
ord-5505fad798d240c99a94a469200847b5
Source dataset
uspto-grants-2012_07
Patent number
US08216489B2

Reaction notes

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