Water → HCID 12922709, compound

HRID 2286052Notes

Reaction equation

HRID 2286052 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12](Br)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([O-:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Na+].O.C1C2C(=CC=CC=2)C=CN=1>C1CCCCC1.[Cu-]=O>[CH2:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([O:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8405IsoquinolineHCID 4445035Phenolate SodiumHCID 12922708HCID 12922708, compound

Product 1

HCID 12922709HCID 12922709, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 8078CyclohexaneSolvent

Procedure

A mixture of 1 mol of 3-bromo-4-fluoro-benzyl benzyl ether, 1.1 mol of sodium phenolate, 0.12 mol of copper(I) oxide, 80 g of 4 MgCO3.Mg(OH)2.4 H2O and 1,500 ml of isoquinoline was heated to 160° C. for 12 hours. The reaction mixture was then cooled, diluted with cyclohexane and filtered. The filtrate was washed with dilute hydrochloric acid and water, dried over sodium sulphate and filtered and the filtrate was distilled. 4-Fluoro-3-phenoxy-benzyl benzyl ether was obtained in the form of a yellow oil of boiling point 135° C./1 mbar in a yield of 75% of theory.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with dilute hydrochloric acid and water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. distillationthe filtrate was distilled

Sources & evidence

ORD record
ord-f576d3a0b45142eaa37f7a8892079bb6
Source dataset
uspto-grants-1982_04
Patent number
US04326087

Reaction notes

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