Hydrochloric Acid → HCID 67584087, compound

HRID 1941032Notes

Reaction equation

HRID 1941032 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Br:13])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[CH2:14]1[O:16][CH2:15]1.Cl.O>CCOCC>[F:1][CH:2]1[C:7]([O:8][C:9]([F:10])([F:11])[F:12])([O:16][CH2:15][CH3:14])[CH:6]=[CH:5][C:4]([Br:13])=[CH:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6354Ethylene OxideHCID 27822174-Bromo-2-fluoro-1-(trifluoromethoxy)benzene

Product 1

HCID 67584087HCID 67584087, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-50 °C

Procedure

A Grignard reagent prepared from 3-fluoro-4-trifluoromethoxyphenylbromide (200.0 g, 772 mmol) and dried Mg (18.8 g, 774 mmol) in ether was cooled down to -50° C. in a nitrogen atmosphere, followed by dropwise adding thereto a 100 ml ether solution of ethylene oxide (100 g, 2.27 mol), stirring the reaction solution at 0° C. for 2 hours, adding the resulting reaction product to 6N HCl, extracting the product with toluene, washing the extraction solution successively a saturated aqueous solution of sodium bicarbonate and water, drying over the organic layer over magnesium sulfate, distilling off the solvent, adding to the residue, 47% hydrogen bromic acid (300 ml) and xylene (300 ml), refluxing the mixture for 9 hours, while removing water formed by the reaction by means of Dean-Stark, adding water (500 ml) to the resulting reaction product, extracting the resulting product with toluene, washing the extraction solution successively with a saturated aqueous solution of sodium bicarbonate and water, distilling off the solvent, and distilling the residue under reduced pressure, to obtain 3-fluoro-4-trifluoromethoxyphenetylbromide (68.3 g, 238 mmol). Yield: 30.7%.

Workup

  1. additionby dropwise adding
  2. additionadding
  3. extractionextracting the product with toluene
  4. washwashing the extraction solution successively a saturated aqueous solution of sodium bicarbonate and water
  5. dry with materialdrying over the organic layer over magnesium sulfate
  6. distillationdistilling off the solvent
  7. additionadding to the residue, 47% hydrogen bromic acid (300 ml) and xylene (300 ml)
  8. temperaturerefluxing the mixture for 9 hours
  9. customwhile removing water
  10. customformed by the reaction by means of Dean-Stark
  11. customto the resulting reaction product
  12. extractionextracting the resulting product with toluene
  13. washwashing the extraction solution successively with a saturated aqueous solution of sodium bicarbonate and water
  14. distillationdistilling off the solvent
  15. distillationdistilling the residue under reduced pressure

Sources & evidence

ORD record
ord-11203aeefd944661bfa73c03a5964791
Source dataset
uspto-grants-1997_12
Patent number
US05702641

Reaction notes

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