Hydrochloric Acid → 4-(4-Bromo-3-formylphenoxy)-3-hydroxybenzonitrile

HRID 1483631Notes

Reaction equation

HRID 1483631 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[O:15]COC)=[CH:4][C:3]=1[CH:21]1OCC[O:22]1.Cl.O>O1CCCC1>[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[OH:15])=[CH:4][C:3]=1[CH:21]=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 674390784-(4-Bromo-3-(1,3-dioxolan-2-yl)phenoxy)-3-methoxymethoxybenzonitrile

Product 1

HCID 866364134-(4-Bromo-3-formylphenoxy)-3-hydroxybenzonitrileYield 102.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-bromo-3-(1,3-dioxolan-2-yl)phenoxy)-3-methoxymethoxybenzonitrile (32.2 g, 79.3 mmol) in tetrahydrofuran (300 mL) was added 3 M HCl (100 mL), and the mixture was refluxed for 2 h. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 4-(4-bromo-3-formylphenoxy)-3-hydroxybenzonitrile (25.8 g, quant.).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-72c8306491554a70bf8d923abfcf3d55
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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