Magnesium Carbonate → 1-Fluoro-4-methyl-2-phenoxybenzene

HRID 1447473Notes

Reaction equation

HRID 1447473 reaction equation
C(=O)([O-])[O-].[Mg+2].[C:6]1([O-:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Na+].Br[C:15]1[CH:16]=[C:17]([CH3:22])[CH:18]=[CH:19][C:20]=1[F:21]>C1C2C(=CC=CC=2)C=CN=1.[Cu-]=O>[F:21][C:20]1[CH:19]=[CH:18][C:17]([CH3:22])=[CH:16][C:15]=1[O:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 11029Magnesium CarbonateHCID 967453-Bromo-4-fluorotolueneHCID 4445035Phenolate Sodium

Product 1

HCID 142572981-Fluoro-4-methyl-2-phenoxybenzeneYield 84.1%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 8405IsoquinolineSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 84.3 g of magnesium carbonate (4MgCO3 .Mg(OH)2.4H2O) and 128 g (1.1 mol) of sodium phenolate was added to a suspension of 189 g (1 mol) of 3-bromo-4-fluoro-toluene and 50 g of copper(I) oxide in 250 ml of isoquinoline at 110° C. The reaction temperature was then increased to 160° C. and the mixture was subsequently stirred at this temperature for 15 hours. Thereafter, the reaction mixture was cooled and filtered. The filtrate was taken up in cyclohexane. The cyclohexane solution was washed with hydrochloric acid and water, dried over sodium sulphate and then concentrated. After distillation of the residue, 170 g (84.1% of theory) of 4-fluoro-3-phenoxy-toluene were obtained in the form of a pale yellow oil of boiling point 105° C./6 mbars.

Workup

  1. temperatureThereafter, the reaction mixture was cooled
  2. filtrationfiltered
  3. washThe cyclohexane solution was washed with hydrochloric acid and water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. distillationAfter distillation of the residue

Sources & evidence

ORD record
ord-56d8260b82b648fdb6653950672a8252
Source dataset
uspto-grants-1982_02
Patent number
US04316994

Reaction notes

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