Sodium Carbonate → 3'-Chloro-3-nitro-4'-trifluoromethyl-biphenyl-4-ylamine

HRID 2098238Notes

Reaction equation

HRID 2098238 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[C:19]([F:22])([F:21])[F:20].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:12][C:13]1[CH:14]=[C:15]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=2)[CH:16]=[CH:17][C:18]=1[C:19]([F:20])([F:21])[F:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 701324-Bromo-2-nitroanilineHCID 37729583-Chloro-4-(trifluoromethyl)benzeneboronic acid

Product 1

HCID 673869773'-Chloro-3-nitro-4'-trifluoromethyl-biphenyl-4-ylamineYield 101.1%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
95 °C

Procedure

A mixture of 4-bromo-2-nitroaniline (2.17 g), 3-chloro-4-trifluoromethyl-phenylboronic acid (3.5 g), and Na2CO3 (3.5 g), tetrakis(triphenylphosphine)palladium(0) (0.5 g), in DME (60 mL) and water (60 mL) was degassed under vacuum and the vacuum was broken with N2 gas. The resultant reaction mixture was kept stirring at 90-100° C. for 4 h. The reaction mixture was cooled to room temperature, separated the organic layer and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was dried over sodium sulfate, filtered off sodium sulfate, the filtrate was concentrated and the residue was purified by column chromatography using a silica gel stationary phase and ethyl acetate in hexanes (2:8) as an eluent to afford 3′-chloro-3-nitro-4′-trifluoromethyl-biphenyl-4-ylamine (3.2 g).

Workup

  1. customin DME (60 mL) and water (60 mL) was degassed under vacuum
  2. customThe resultant reaction mixture
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customseparated the organic layer
  5. extractionthe aqueous layer was extracted with ethyl acetate (100 mL)
  6. dry with materialThe combined organic layer was dried over sodium sulfate
  7. filtrationfiltered off sodium sulfate
  8. concentrationthe filtrate was concentrated
  9. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b521901c2dc04e9ba7eed6a2af09a046
Source dataset
uspto-grants-2013_05
Patent number
US08450354B2

Reaction notes

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