Hydrochloric Acid → HCID 66986038, compound

HRID 2069910Notes

Reaction equation

HRID 2069910 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])[C:5]#[N:6].Cl>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])[CH2:5][NH2:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 114034163-Bromo-4-[(2-methoxyethoxy)methoxy]benzonitrile

Product 1

HCID 66986038HCID 66986038, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Borane-tetrahydrofuran complex (280 mL, 1 M, 280 mmol) was added to a magnetically stirred solution of 3-bromo-4-(2-methoxyethoxymethoxy)-benzonitrile (10 g, 35 mmol) in tetrahydrofuran (20 mL) and the reaction mixture was refluxed for 30 minutes. The mixture was cooled to 0° C. and 1 N HCl was added very slowly until the pH was acidic. The tetrahydrofuran was removed by evaporation and the residual aqueous layer was washed with ethyl ether. The aqueous extract was basified with 2 N sodium hydroxide until alkaline pH and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated by evaporation to give 3-bromo-4-(2-methoxy-ethoxymethoxy)benzylamine (5.6 g).

Workup

  1. temperaturethe reaction mixture was refluxed for 30 minutes
  2. customThe tetrahydrofuran was removed by evaporation
  3. washthe residual aqueous layer was washed with ethyl ether
  4. extractionThe aqueous extract
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1aab5edd3d2848f09420073485754d77
Source dataset
uspto-grants-2012_10
Patent number
US08299110B2

Reaction notes

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