1-Bromopentane → 4-Bromo-4'-(pentyloxy)-1,1'-biphenyl

HRID 264598

Reaction equation

HRID 264598 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH3:21]>CS(C)=O>[CH2:17]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 14798Sodium HydroxideHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 28013884-Bromo-4'-(pentyloxy)-1,1'-biphenylYield 94.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 4-(4-bromophenyl)phenol (25.5 g, 0.102 mol) in 400 mL of dimethylsulfoxide was added 2.5N NaOH (40.9 ml, 0.102 mol) followed by n-pentyl bromide (12.7 mL, 0.102 mol). The resulting mixture was heated at 70° C. for a period of 18 h. After cooling, the solution was partitioned between ethyl acetate (1000 ml) and water (500 ml). The organic phase was washed with water (3×) and brine and dried with magnesium sulfate. The solvent was removed in vacuo to give 30.9 g of 4-(4-n-pentoxyphenyl)-bromobenzene: 1H NMR (400 MHz, DMSO-d6) δ0.93 (t, 3H, J=7.2 Hz), 1.41 (m, 4H), 1.79 (m, 2H), 3.97 (t, 2H, J=6.6 Hz), 6.94 (d, 2H, J=8.8 Hz), 7.39 (d, 2H, J=8.6 Hz), 7.45 (d, 2H, J=8.8 Hz), 7.51 (d, 2H, J=8.6 Hz).

Workup

  1. temperatureAfter cooling
  2. customthe solution was partitioned between ethyl acetate (1000 ml) and water (500 ml)
  3. washThe organic phase was washed with water (3×) and brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f42f3121e17c417fafcf6c21f54242d3
Source dataset
uspto-grants-1997_07
Patent number
US05646245

Linked notes

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