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

HRID 1664318Notes

Reaction equation

HRID 1664318 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-992d5d9d30964dd79fe9893fa19bacd7
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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