1-Bromo-4-fluorobenzene → 4-Fluorobiphenyl

HRID 2407469Notes

Reaction equation

HRID 2407469 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[F:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C(O)CC.[Pd]>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic Acid

Product 1

HCID 94614-Fluorobiphenyl

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 10311-PropanolSolvent

Conditions

Temperature
85 °C

Procedure

A solution of sodium carbonate (3.3 g, 0.031 mol) in demineralized water (25 mL) is added to a solution containing 4-fluorobromobenzene (4.55 g, 0.026 mol), phenylboronic acid (3.3 g, 0.027 mol), Pd (II) acetate (18 mg) and triphenylphosphine (65 mg) in n-propanol (50 mL). The reaction mixture is stirred at 80-90° C. for 1 hour. It is allowed to cool back to room temperature. Demineralized water (100 mL) is added and the aqueous layer is extracted with ethyl acetate (200 mL). The organic layer is concentrated and the residue is purified by column chromatography (silica gel 230-400 mesh, ethyl acetate:n-hexane 10:90) to furnish 4-fluorobiphenyl.

Workup

  1. temperatureto cool back to room temperature
  2. extractionthe aqueous layer is extracted with ethyl acetate (200 mL)
  3. concentrationThe organic layer is concentrated
  4. customthe residue is purified by column chromatography (silica gel 230-400 mesh, ethyl acetate:n-hexane 10:90)

Sources & evidence

ORD record
ord-b011012519514cb1bbfe53eb8cb7446d
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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