Potassium Carbonate → N-(2-bromo-6-chloro-4-(trifluoromethyl)benzyl)-2',4'-dichloro-[1,1'-biphenyl]-4-amine

HRID 405189Notes

Reaction equation

HRID 405189 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([Cl:14])[C:3]=1[CH:4]=O.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.CC(O)=O.ClCCCl>[Br:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([Cl:14])[C:3]=1[CH2:4][NH:29][C:26]1[CH:25]=[CH:24][C:23]([C:17]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[Cl:15])=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 99647252',4'-Dichloro-[1,1'-biphenyl]-4-amineHCID 866742632-Bromo-6-chloro-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 86674262N-(2-bromo-6-chloro-4-(trifluoromethyl)benzyl)-2',4'-dichloro-[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A DCE solution (33 mL) of 2-bromo-6-chloro-4-(trifluoromethyl)benzaldehyde (3.7 g, 12.9 mmol), 2′,4′-dichloro-[1,1′-biphenyl]-4-amine (3.4 g, 14.4 mmol), and HOAc (3.0 mL) was heated to 70° C. After 10 min the homogeneous solution was cooled to room temperature and solid NaBH(OAc)3 (5.46 g, 25.8 mmol) was added and the resulting mixture was warmed to 40° C. After 30 min, EtOAc and 2 M K2CO3 were added and the layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with 4 M NaCl, dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. temperaturethe resulting mixture was warmed to 40° C
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with 4 M NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified via column chromatography

Sources & evidence

ORD record
ord-0aa8328cf29846d98121f0bb3f721d1e
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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