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Benzene → 2'-Trifluoromethyl-biphenyl-4-ylamine

HRID 1062658
Notes
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Reaction equation

HRID 1062658 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([F:21])([F:20])[F:9])=[CH:3][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 241BenzeneHCID 78074-BromoanilineHCID 10340Sodium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acid

Product 1

HCID 27607432'-Trifluoromethyl-biphenyl-4-ylamineYield 44.1%

Reagents, catalysts & solvents 4

HCID 74236
Tetrabutylammonium Bromide
Catalyst
HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.44 g (20 mmol) of 4-bromoaniline and 3.80 g (20 mmol) of 2-(trifluoromethyl)phenylboronic acid, 1.16 g of tetrakis(triphenylphosphine) palladium(0) (1 mmol), 0.32 g of tetrabutylammonium bromide (1 mmol) and 20 mL of 2M aqueous sodium carbonate were refluxed with 180 mL of benzene under N2 for 14 hours. After cooling, the mixture was diluted with methylene chloride and water. The two phases were separated and the organic phase was washed with water, dried with MgSO4 and concentrated in vacuo. The resulting thick oil was chromatographed on silica with 10% EtOAc/hexane to afford 2.09 g (44%) of the aniline. 1H NMR (CDCl3) δ: 7.72 (d, 1H); 7.53 (t, 1H); 7.41 (t, 1H); 7.32 (d, 1H); 7.13 (d, 2H); 6.73 (d, 2H); 3.74 (br s, 2H).

Workup

  1. temperatureAfter cooling
  2. customThe two phases were separated
  3. washthe organic phase was washed with water
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting thick oil was chromatographed on silica with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-b9e435c589424f25a57dc694b27f6c90
Source dataset
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06962935B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes