1,2-Dimethoxyethane → 4-(4-(Trifluoromethoxy)phenyl)pyridine

HRID 1107288

Reaction equation

HRID 1107288 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1.Cl.Br[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>O.C1(P(CCCC[Pd-](Cl)Cl)C2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 27343864-(Trifluoromethoxy)phenylboronic acid

Product 1

HCID 187870514-(4-(Trifluoromethoxy)phenyl)pyridine

Reagents, catalysts & solvents 2

HCID 178479790HCID 178479790, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-(trifluoromethoxy)benzene boronic acid (2 g, 9.7 mmol), 4-bromopyridine hydrochloride (2.83 g, 14.5 mmol), diphenylphosphinobutylpalladium (II) dichloride (100 mg), dimethoxyethane (50 ml) and a 2M sodium carbonate solution (30 ml) were stirred at 85° C. for 2 hours. The solution was allowed to cool to ambient temperature diluted with water (100 ml), and extracted with ethyl acetate (2×100 ml). The combined organic layers were dried over sodium sulphate. Removal of the solvents in vacuo gave an oil which was chromatographed on silica in 30% ethyl acetate/hexane giving the title compound as an oil (1.86 g, 80%). 1H NMR (250 MHz, CDCl3) δ 8.72-8.70 (2H, d, J=6.2 Hz), 7.69-7.63 (2H, d, J=9.6 Hz), 7.49-7.47 (2H, d, J=6.2 Hz), and 7.36-7.32 (2H, d, J=9.6 Hz). m/z (ES+) 240 (M+1).

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customRemoval of the solvents in vacuo
  4. customgave an oil which
  5. customwas chromatographed on silica in 30% ethyl acetate/hexane giving the title compound as an oil (1.86 g, 80%)

Sources & evidence

ORD record
ord-cd14e6b7c3c444f3a6ac9cdadea5b074
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Linked notes

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