Water → 1-Bromo-4-butoxybenzene

HRID 2120036Notes

Reaction equation

HRID 2120036 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:11](Br)[CH2:12][CH2:13][CH3:14].O>C(O)C>[CH2:11]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 8002Butyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 1423951-Bromo-4-butoxybenzeneYield 78.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 200 g of ethanol were dissolved 86.5 g (0.5 mol) of 4-bromophenol and 22 g (0.55 mol) of sodium hydroxide. To the solution at 70° C., 75.4 g (0.55 mol) of n-butyl bromide was added dropwise. The solution was allowed to ripen for 4 hours and cooled to room temperature, after which 120 g of water was added. The oily matter was separated therefrom and concentrated by a rotary evaporator, yielding 90 g of 4-n-butoxyphenyl bromide. This was used in the subsequent reaction without further purification.

Workup

  1. customThe oily matter was separated
  2. concentrationconcentrated by a rotary evaporator

Sources & evidence

ORD record
ord-83e8b01dd43c40fc92dd4c83a5ed49aa
Source dataset
uspto-grants-2004_02
Patent number
US06689530B2

Reaction notes

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