Acetic Acid → HCID 10979104, compound

HRID 1585227Notes

Reaction equation

HRID 1585227 reaction equation
[Br:1][C:2]([F:16])([F:15])[C:3]([F:14])([F:13])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11]C.C(O)(=O)C.Br>O>[Br:1][C:2]([F:15])([F:16])[C:3]([F:13])([F:14])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 10979585HCID 10979585, compound

Product 1

HCID 10979104HCID 10979104, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 54.42 g of 1-(2-bromo-1,1,2,2-tetrafluoroethoxy)-2-methoxybenzene in 500 ml of an acid mixture of acetic acid (96% by weight)/hydrobromic acid (48% by weight) 2.5:1 was stirred for 43 hours under reflux, the completeness of the reaction being monitored by gas chromatography (GC). The reaction mixture was then cooled to 20° C. and poured into water. The organic phase was separated off and the aqueous phase was extracted twice with dichloromethane. The extracts were added to the organic phase, and the mixture was dried over magnesium sulfate and evaporated in vacuo. Distillation of the residue gave 43.55 g (83.9% of theory) of 2-(2-bromo-1,1,2,2-tetrafluoroethoxy)-phenol of boiling point 84° C./20 mbar.

Workup

  1. temperatureunder reflux
  2. customThe organic phase was separated off
  3. extractionthe aqueous phase was extracted twice with dichloromethane
  4. additionThe extracts were added to the organic phase
  5. dry with materialthe mixture was dried over magnesium sulfate
  6. customevaporated in vacuo
  7. distillationDistillation of the residue

Sources & evidence

ORD record
ord-435ba8041b844997a0560b70a0cc6189
Source dataset
uspto-grants-1999_08
Patent number
US05936102

Reaction notes

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