4-Hydroxybiphenyl → 1,1'-Biphenyl, 4-(3-bromopropoxy)-

HRID 533851Notes

Reaction equation

HRID 533851 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][C:4]([OH:7])=[CH:3][CH:2]=1.[Br:14][CH2:15][CH2:16][CH2:17]Br.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[Br:14][CH2:15][CH2:16][CH2:17][O:7][C:4]1[CH:3]=[CH:2][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 80011,3-DibromopropaneHCID 10796Cesium carbonate

Product 1

HCID 152334631,1'-Biphenyl, 4-(3-bromopropoxy)-Yield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-biphenylol (0.0514 g, 0.302 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.310 mL, 3.05 mmol) followed by Cs2CO3 (0.154 g, 0.472 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DCM (8 mL). The organic layer was dried through a phase separator and concentrated under vacuum. The residue was taken up in DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.0562 g, 64.0%). EI-MS Rt (2.62 min).

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe resulting residue was treated with H2O (4 mL)
  3. extractionextracted with DCM (8 mL)
  4. customThe organic layer was dried through a phase separator
  5. concentrationconcentrated under vacuum
  6. custompurified by preparatory HPLC (without TFA)

Sources & evidence

ORD record
ord-94df8549172e47339fbb9013d5d543c2
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Reaction notes

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