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

HRID 554619Notes

Reaction equation

HRID 554619 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

2-Bromo-5-(trifluoromethyl)benzaldehyde (20 g, 79.1 mmol), ethylamine (2M in MeOH; 59.3 mL, 118.6 mmol), and sodium cyanoborohydride (7.45 g, 118.6 mmol) were combined in MeOH (200 mL). Acetic acid (6.79 mL, 118.6 mmol) was added, and the reaction was stirred at room temperature overnight. The mixture was concentrated and partitioned between CH2Cl2 and H2O. The aqueous layer was separated and extracted twice with CH2Cl2, and the combined organic layers were dried over Na2SO4 and concentrated to give (2-bromo-5-trifluoromethyl-benzyl)-ethyl-amine.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between CH2Cl2 and H2O
  3. customThe aqueous layer was separated
  4. extractionextracted twice with CH2Cl2
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4901b16594974cc293ee00348a0edac3
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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