Hydrochloric Acid → HCID 53401484, compound

HRID 468718Notes

Reaction equation

HRID 468718 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH:9]=1)[C:7]#[N:8].B.C1COCC1.Cl.[OH-].[K+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH2:7][NH2:8])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 70208745-Bromo-2-iodobenzonitrile

Product 1

HCID 53401484HCID 53401484, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-2-iodobenzonitrile (9.21 g, 0.03 mol) in tetrahydrofuran (140 mL) at 0° C. was added BH3-THF (66 mL, 66 mmol, 1 M solution in tetrahydrofuran) dropwise over 1 hour. The reaction solution was stirred at room temperature for 10 minutes, and then heated to reflux for overnight. 10% aqueous HCl was added (to adjust to pH 2-3) and stirred for 20 minutes, then the mixture was basified with 10 M aqueous KOH up to pH>10. The mixture was extracted with ethyl acetate three times. Organics were combined, dried with sodium sulfate, filtered and concentrated in vacuo to yield 6.2 g of crude (5-bromo-2-iodophenyl)methanamine as a yellow oil. LCMS (ESI): M+H=311.7; 1H NMR (400 MHz, DMSO-d6): δ 7.71 (d, J=8.4 Hz, 1H), 7.67 (d, J=2.4 Hz, 1H), 7.18 (dd, J=2.4, 8.4 Hz, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for overnight
  3. stirringstirred for 20 minutes
  4. extractionThe mixture was extracted with ethyl acetate three times
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a07ee721a3f3426a8e49fb22b7ad7d59
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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