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

HRID 1736289Notes

Reaction equation

HRID 1736289 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 yellow 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 4-(4-n-pentoxyphenyl)bromobenzene (30.9 g).

Workup

  1. temperatureAfter cooling
  2. customthe yellow 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-ab39e8d72e3a4ec28f55f8ba7ae9026f
Source dataset
uspto-grants-1996_07
Patent number
US05541160

Reaction notes

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