Hydrochloric Acid → HCID 57445079, compound

HRID 558130Notes

Reaction equation

HRID 558130 reaction equation
C[Si]([C:5]#[N:6])(C)C.[Br:7][C:8]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.[I-].[I-].[Zn+2]>[NH2:6][CH2:5][CH:10]([C:9]1[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:8]=1[Br:7])[OH:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 82115Trimethylsilyl cyanideHCID 27733192-Bromo-4-fluorobenzaldehyde

Product 1

HCID 57445079HCID 57445079, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

Add trimethylsilyl cyanide (1.01 mL, 7.39 mmol) and zinc diiodide (0.11 g, 0.37 mmol) to a solution of 2-bromo-4-fluorobenzaldehyde (1.5 g, 7.39 mmol) in DCM (10 mL). Stir the mixture overnight at RT. Remove the solvent. Dissolve the residue in THF (5 mL) and cool at 0° C. Add borane-THF complex (11.1 mL, 11.1 mmol). Stir the mixture at RT for 3 h. Add 1 M HCl slowly and stir for 15 min. Adjust the pH to basic with saturated sodium carbonate. Extract with DCM. Dry it over sodium sulfate and concentrate to give the title compound as a colorless oil (1.5 g, 86%). MS (ES) m/z 235 [M+1]+.

Workup

  1. customRemove the solvent
  2. dissolutionDissolve the residue in THF (5 mL)
  3. temperaturecool at 0° C
  4. stirringStir the mixture at RT for 3 h
  5. stirringstir for 15 min
  6. extractionExtract with DCM
  7. dry with materialDry it over sodium sulfate
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-1bf30752434d4c91a9023986a67364ee
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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