4-Bromophenol → 1-(4-Bromophenoxy)-2-nitrobenzene

HRID 449106

Reaction equation

HRID 449106 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O)([O-:11])=[O:10]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78084-BromophenolHCID 2773548(2-Nitrophenyl)boronic acid

Product 1

HCID 2542611-(4-Bromophenoxy)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100 mL round bottom flask was added 4-bromophenol (2.07 g, 12.0 mmol), 2-nitrophenylboronic acid (1.00 g, 5.99 mmol), cupric acetate (1.4 g, 7.70 mmol) and DCM (50 mL). TEA (4.0 mL, 29.0 mmol) was then added followed by 4 A° molecular sieves and the reaction mixture 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.

Workup

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

Sources & evidence

ORD record
ord-a115ccf9a179472085f2c7d84a9182e6
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Linked notes

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