Acetic Acid → (5-Bromo-2-iodo-benzyl)-ethyl-amine

HRID 2197336Notes

Reaction equation

HRID 2197336 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH:9]=1)[CH:7]=O.[CH2:11]([NH2:13])[CH3:12].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH:9]=1)[CH2:7][NH:13][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 219738615-Bromo-2-iodobenzaldehyde

Product 1

HCID 58148919(5-Bromo-2-iodo-benzyl)-ethyl-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5-bromo-2-iodo-benzaldehyde (5.0 g, 16.1 mmol) in MeOH (20 mL) was added ethylamine (2M in MeOH; 16 mL, 24.0 mmol), followed by acetic acid (1.0 mL, 17.8 mmol), and the mixture was stirred at room temperature for 30 minutes. Sodium cyanoborohydride (2.0 g, 31.8 mmol) was then added over 5 minutes, and the reaction was stirred at room temperature over the weekend. The mixture was concentrated and partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give the title compound.

Workup

  1. stirringthe reaction was stirred at room temperature over the weekend
  2. concentrationThe mixture was concentrated
  3. custompartitioned between EtOAc and saturated aqueous NaHCO3
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6221b05354c4423a9b49036783290477
Source dataset
uspto-grants-2012_12
Patent number
US08338484B2

Reaction notes

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