Acetic Acid → HCID 67212329, compound

HRID 554629Notes

Reaction equation

HRID 554629 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]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:14]([NH:21][CH2:4][C:3]1[CH:6]=[C:7]([C:10]([F:13])([F:12])[F:11])[CH:8]=[CH:9][C:2]=1[Br:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 70180472-Bromo-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 67212329HCID 67212329, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Bromo-5-(trifluoromethyl)benzaldehyde (3 g, 11.9 mmol), benzylamine (1.94 mL, 17.8 mmol), and sodium cyanoborohydride (1.12 g, 17.8 mmol) were combined in MeOH (30 mL). Acetic acid (1.02 mL, 17.8 mmol) was added, and the reaction was stirred at room temperature for 2 hours. The mixture was concentrated, and the residue was partitioned between CH2Cl2 and H2O. The aqueous layer was separated and extracted twice with CH2Cl2, and the combined organic layers were dried, concentrated, and purified by silica gel chromatography (10-40% EtOAc in hexanes) to give benzyl-(2-bromo-5-trifluoromethyl-benzyl)-amine.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between CH2Cl2 and H2O
  3. customThe aqueous layer was separated
  4. extractionextracted twice with CH2Cl2
  5. customthe combined organic layers were dried
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (10-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9eadc648d33a490d9c3f9d8e1a43d4e4
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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