4-Fluorophenol → 1-fluoro-2-(4-fluorophenoxy)benzene

HRID 446692Notes

Reaction equation

HRID 446692 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[K+].Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18]>[Cu]>[CH:16]1[CH:15]=[C:14]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:13]([F:18])=[CH:12][CH:17]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 14797Potassium HydroxideHCID 612591-Bromo-2-fluorobenzene

Product 1

HCID 212008881-fluoro-2-(4-fluorophenoxy)benzene

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

4-Fluorophenol (1.12 g, 10 mmol) was heated to 50° C. KOH (0.56 g, 10 mmol) was added thereto, and the reaction mixture was stirred over 10 min. 2-Bromofluorobenzene (1.75 g, 10 mmol) and powdered copper (0.64 g) were added thereto. The reaction mixture was stirred at 110° C. over a further 2 hours. Unconverted 2-bromofluorobenzene was removed by means of vacuum distillation. The product was subsequently purified on a silica gel-packed column with n-hexane as the mobile phase. Yield: 1.0 g (4.8 mmol, 48%) of the product with a purity of 97.3%, determined by means GC. 1H NMR: δ 6.92-7.21 multiple peaks. 13C NMR: δ 158.0 (d, 1JC-F=341.2, C-4′), 154.8 (d, 1JC-F=348.5, C-2), 153.2 (d, 4JC-F=3.1, C-1′), 144.2 (d, 2JC-F=11.3, C-1), 124.7 (m, C-6, C-2′ and C-6′), 121.3 (d, 4JC-F=1.7, C-5), 118.9 (d, 3JC-F=8.3, C-4), 117.1 (d, 2JC-F=18.3, C-3), 116.2 (d, 2JC-F=23.8, C-3′ and C-5′).

Workup

  1. stirringThe reaction mixture was stirred at 110° C. over a further 2 hours
  2. customUnconverted 2-bromofluorobenzene was removed by means of vacuum distillation
  3. customThe product was subsequently purified on a silica gel-

Sources & evidence

ORD record
ord-c6d3b69c5539432f819688d7e8c165cb
Source dataset
uspto-grants-2013_07
Patent number
US08481327B2

Reaction notes

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