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

HRID 2232957Notes

Reaction equation

HRID 2232957 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+].I[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 123351-IodopentaneHCID 14798Sodium HydroxideHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 28013884-Bromo-4'-(pentyloxy)-1,1'-biphenyl

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4-Bromo-4′-hydroxybiphenyl (12.5 g, 50.2 mmol) was added to a solution of NaOH (2.28 g, 97% pure, 55.2 mmol) in deionized H2O (150 ml), followed by the addition of 1-iodopentane (11.9 g, 60.2 mmol) and tetrabutylammonium bromide (0.82 g, 2.51 mmol). The mixture was stirred at 90° C. for 3.75 h until the solids went into solution. Then, as the reaction proceeded, the desired product began to precipitate. The mixture was slowly cooled and then filtered to provide a solid which was washed with deionized water until the pH of the filtrate was neutral and then dried for 16 h in a vacuum oven at 30° C.

Sources & evidence

ORD record
ord-bf97ed374bc84534908007842fff3244
Source dataset
uspto-grants-2010_05
Patent number
US07709444B2

Reaction notes

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