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

HRID 1919977Notes

Reaction equation

HRID 1919977 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-b0aaf92cab3f49a0b7e95a3278ac2a73
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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