Hydrochloric Acid → 3,5-Dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenol

HRID 260783Notes

Reaction equation

HRID 260783 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:21]CC2C=CC=CC=2)[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=1.B(Br)(Br)Br.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([OH:21])[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:17])[F:18])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 214665743,5-Dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-1-benzyloxybenzene

Product 1

HCID 153762963,5-Dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenolYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Then, 1.39 g of 3,5-dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-1-benzyloxybenzene and 20 ml of methylene chloride were charged into a reaction vessel, and a solution of boron tribromide (1.63 g) in methylene chloride (10 ml) was added dropwise with stirring under ice cooling (-10° C. to 0° C.). After stirring for one hour under ice cooling, the mixture was poured into 10% hydrochloric acid and extracted twice with 50 ml of methylene chloride. Then, the organic layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give a crude product. This crude product was subjected to silica gel column chromatography to give 1.03 g of 3,5-dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenol (yield, 93%), m.p., 152.6° C.

Workup

  1. stirringAfter stirring for one hour under ice cooling
  2. extractionextracted twice with 50 ml of methylene chloride
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give a crude product

Sources & evidence

ORD record
ord-39f3d494a5b745a6a36bc80206c2012f
Source dataset
uspto-grants-1996_06
Patent number
US05530015

Reaction notes

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