Tetrafluoroboric acid → 1-Fluoro-3,5-dimethoxybenzene

HRID 1798042Notes

Reaction equation

HRID 1798042 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](N)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[F:12][B-](F)(F)F.[H+].N([O-])=O.[Na+]>O>[F:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=1

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 663013,5-DimethoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 27742571-Fluoro-3,5-dimethoxybenzeneYield 48.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3,5-dimethoxybenzenamine (6.12 g, 40.0 mmol) and tetrafluoroboric acid (8% solution, 70 mL) was added dropwise a solution of sodium nitrite (2.84 g, 41.2 mmol) in water (10 mL). After stirring at room temperature for 30 min, the reaction mixture was filtered. The solid was collected and washed with water (2×10 mL) and dried under high vacuum. The resulting red solid was suspended in dry hexane (50 mL) and heated to reflux for 2 hr. The mixture was filtered and the filtrate was concentrated to give the crude product as a yellow oil (3.03 g, Yield: 48.5%). MS (ESI) m/z=157 [M+H]+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customThe solid was collected
  3. washwashed with water (2×10 mL)
  4. customdried under high vacuum
  5. temperatureheated
  6. temperatureto reflux for 2 hr
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-33db65aabbae4509a6b76e260db21a1c
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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