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Potassium Phosphate, Tribasic → 2-Fluoro-4-(4-methoxy-2-trifluoromethyl-phenylamino)-benzonitrile

HRID 1428202
Notes
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Reaction equation

HRID 1428202 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.Br[C:57]1[CH:64]=[CH:63][C:60]([C:61]#[N:62])=[C:59]([F:65])[CH:58]=1>C1(C)C=CC=CC=1>[F:65][C:59]1[CH:58]=[C:57]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[C:10]([F:11])([F:12])[F:13])[CH:64]=[CH:63][C:60]=1[C:61]#[N:62]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 7360294-Bromo-2-fluorobenzonitrileHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 226017214-Methoxy-2-(trifluoromethyl)aniline

Product 1

HCID 667656782-Fluoro-4-(4-methoxy-2-trifluoromethyl-phenylamino)-benzonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

2-Amino-5-methoxy-benzotrifluoride (10.46 mmol), K3PO4 (15.7 mmol), Xphos (1.05 mmol) and Pd4(dba)3 (0.314 mmol) were added under nitrogen to a solution of 4-bromo-2-fluoro-benzonitrile (10.46 mmol) in 50 mL toluene and the mixture was stirred for 20 hours at a bath temperature of 110° C. Then the mixture was filtered through a glass fibre filter, then the filtrate was extracted with 150 mL water. The organic phase was dried on sodium sulphate and evaporated down. In this way the product was obtained in a yield of 87% of theory.

Workup

  1. filtrationThen the mixture was filtered through a glass fibre
  2. filtrationfilter
  3. extractionthe filtrate was extracted with 150 mL water
  4. customThe organic phase was dried on sodium sulphate
  5. customevaporated down
  6. customIn this way the product was obtained in a yield of 87% of theory

Sources & evidence

ORD record
ord-16fef055e3bb4594b4fe0f5f07f37451
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937073B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes