Phenylboronic Acid → 1-Bromo-2,5-difluoro-4-phenoxybenzene

HRID 449097Notes

Reaction equation

HRID 449097 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([O:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 70180424-Bromo-2,5-difluorophenol

Product 1

HCID 669156731-Bromo-2,5-difluoro-4-phenoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-2,5-difluorophenol (500 my, 0.002 mol), phenylboronic acid (0.73 g, 0.0060 mol), TEA (2.0 mL, 0.014 mol), cupric acetate (0.70 g, 0.0038 mol) and DCM (20 mL) were added to a 100 mL oven dried flask and the reaction was stirred at rt for 48 h. Reaction mixture was then filtered through celite. The filtrate was concentrated in vacuo to give a residue which was purified by silica gel chromatography, eluting with 5% EtOAc in hexane. 1H NMR (400 MHz, CDCl3): δ=6.81 (dd, J=8.84, 7.07 Hz, 1H), 6.98-7.08 (m, 2H), 7.19 (t, J=7.45 Hz, 1H), 7.31-7.48 (m, 3H).

Workup

  1. customdried flask
  2. customReaction mixture
  3. filtrationwas then filtered through celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a residue which
  6. customwas purified by silica gel chromatography
  7. washeluting with 5% EtOAc in hexane

Sources & evidence

ORD record
ord-f2e34dbc30e0446e935aed0e28fa846a
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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