Water → 3-Bromoanisole

HRID 1902902Notes

Reaction equation

HRID 1902902 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[C:10]1C=CC(O)=CC=1.O>[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([O:8][CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 78084-BromophenolHCID 115633-Bromophenol

Product 1

HCID 169713-BromoanisoleYield 30%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture consisting of 53% of meta bromophenol and 47% of para bromophenol (30.15 g, 0.174 mol) was dissolved in 150 ml of 50% sodium hydroxide and 30 ml of water and cooled to 25° C., whereupon a white solid precipitated. The white solid was filtered and slurried with 20 ml of 50% sodium hydroxide and 5 ml of water. The white solid was then crystallized again in a similar manner and methylated with an excess of dimethylsulfate and sodium hydroxide to yield 9.72 g (30%) of meta bromoanisole after distillation, containing less than 2% of the para isomer.

Workup

  1. customprecipitated
  2. filtrationThe white solid was filtered
  3. customThe white solid was then crystallized again in a similar manner

Sources & evidence

ORD record
ord-482f362825eb47b5a30a1e4b2bc105a3
Source dataset
uspto-grants-1982_12
Patent number
US04366329

Reaction notes

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