Water → 1-(Benzyloxy)-3-bromobenzene

HRID 2399190Notes

Reaction equation

HRID 2399190 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C)C=O>[CH2:11]([O:10][C:6]1[CH:5]=[C:4]([Br:3])[CH:9]=[CH:8][CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 115633-BromophenolHCID 24758Sodium hydride

Product 1

HCID 27566381-(Benzyloxy)-3-bromobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25.43 g (0.64 mol) of a 60% strength by weight sodium hydride dispersion in mineral oil are added in portions at room temperature to 100 g (0.58 mol) of commercially available 3-bromophenol in 600 ml of dimethylformamide, the mixture is stirred for a further half an hour, and 66.5 ml (0.58 mol) of commercially available benzyl chloride are added dropwise. The mixture is stirred at room temperature for 1 hour, 11 of water is added, and the solid which precipitates is filtered off, washed with water and recrystallized from 600 ml of isopropanol, giving 108 g of 3-benzyloxybromobenzene. ##STR12##

Workup

  1. stirringThe mixture is stirred at room temperature for 1 hour
  2. customthe solid which precipitates
  3. filtrationis filtered off
  4. washwashed with water
  5. customrecrystallized from 600 ml of isopropanol

Sources & evidence

ORD record
ord-1b0a31df529846bba3023ca5909c7168
Source dataset
uspto-grants-1995_09
Patent number
US05447656

Reaction notes

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