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

HRID 554605Notes

Reaction equation

HRID 554605 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=O.[CH2:14]([NH2:16])[CH3:15].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH2:4][NH:16][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 70180472-Bromo-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 66603999(2-Bromo-5-trifluoromethyl-benzyl)-ethyl-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2-bromo-5-(trifluoromethyl)benzaldehyde (7.5 g, 29.6 mmol) in MeOH (80 mL) was added ethylamine (2M in MeOH; 30 mL, 60 mmol), sodium cyanoborohydride (3.7 g, 58.9 mmol), and acetic acid (1.7 mL, 26.2 mmol), and the reaction was stirred at room temperature for 4 days. The mixture was quenched with saturated aqueous NaHCO3 and extracted with CH2Cl2, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The crude material was purified by silica gel chromatography (0-4% MeOH in CH2Cl2) to give (2-bromo-5-trifluoromethyl-benzyl)-ethyl-amine.

Workup

  1. customThe mixture was quenched with saturated aqueous NaHCO3
  2. extractionextracted with CH2Cl2
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography (0-4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-bb71bff59c204d94a37433d99e517009
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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