4-Hydroxybiphenyl → 4-(4-Nitrophenoxy)-1,1'-biphenyl

HRID 17729

Reaction equation

HRID 17729 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[OH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.CCOC(C)=O>CN(C=O)C>[C:21]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][C:18]([O:17][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 71034-HydroxybiphenylHCID 8857Ethyl AcetateHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 2408644-(4-Nitrophenoxy)-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-fluoro-4-nitrobenzene (10 mmol) in DMF (20 mL) at room temperature, solid K2CO3 (30 mmol) was added followed by addition of 4-hydroxybiphenyl (10 mmol) to the reaction mixture and heating to 80° C. until the reaction was complete as indicated by TLC or HPLC. After cooling to room temperature to room temperature, the reaction mixture was poured into EtOAc (100 mL), washed with water (2×50 mL) and brine (50 mL), and dried over sodium sulfate. The solvent was removed in vacuo to afford the desired 4-(biphenyl-4-oxy)-1-nitrobenzene. The crude product was used for further transformation.

Workup

  1. temperatureAfter cooling to room temperature to room temperature
  2. washwashed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1bf6e80c0a96446baa085c6ab281ef86
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Linked notes

Loading…