Benzene → HCID 22282493, compound

HRID 1062665Notes

Reaction equation

HRID 1062665 reaction equation
C1C=CC=CC=1.[CH3:7][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.Br[C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[C:21]([F:26])[CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:26][C:21]1[CH:20]=[CH:19][CH:25]=[C:24]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH3:7])[C:22]=1[NH2:23]

Participants

9

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 1230504-Bromo-2-fluoroanilineHCID 27735432-(Methylthio)benzeneboronic acid

Product 1

HCID 22282493HCID 22282493, compoundYield 81%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A benzene solution (100 mL) of 2-methylthiophenylboronic acid (2.07 g, 12.3 mmol); 4-bromo-2-fluoro aniline (1.06 g, 5.6 mmol); aq. Na2CO3 (12.5 mL, 2 M, 25 mmol); and tetra n-butyl ammonium bromide (90 mg, 0.3 mmol) was purged with vacuum and Ar. Bis(triphenylphosphine)palladium (II) chloride (195 mg, 0.3 mmol) was added, and the reaction was refluxed 10 h. After cooling, the reaction was diluted with EtOAc and H2O, the layers were separated, the organic was dried over Na2SO4, filtered, and evaporated. The crude product was chromatographed on silica gel (10% EtOAc/hexanes) to yield the desired product (1.05 g, 81%). 1H NMR (CDCl3) δ: 7.29 (m, 2H); 7.18 (m, 2H); 7.09 (dd, 1H, J=11.7, J′=1.8); 7.01 (dd, 1H, J=8.0, J′=1.4); 6.82 (t, 1H, J=9.2); 3.79 (bs, 2H); 2.38 (s, 3H).

Workup

  1. temperaturethe reaction was refluxed 10 h
  2. temperatureAfter cooling
  3. customthe layers were separated
  4. dry with materialthe organic was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was chromatographed on silica gel (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-087932b965d4429985f12785a0a96b8e
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

Loading…