p-Chlorothiophenol → 2-(4-Chloro-phenylsulfanylmethyl)-1,3,4-trifluoro-benzene

HRID 564299Notes

Reaction equation

HRID 564299 reaction equation
[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[CH2:4]Br.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.C(N(CC)CC)C.C(OCC)(=O)C>C1COCC1.O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH2:4][C:3]2[C:2]([F:1])=[C:9]([F:10])[CH:8]=[CH:7][C:6]=2[F:11])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 7815p-ChlorothiophenolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 5190612,3,6-Trifluorobenzyl bromide

Product 1

HCID 589500982-(4-Chloro-phenylsulfanylmethyl)-1,3,4-trifluoro-benzeneYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,3,6-Trifluorobenzyl bromide (9.79 g, 43.3 mmol) and 4-chlorothiophenol (6.23 g, 43.3 mmol) were dissolved in 300 mL of THF. Triethylamine (4.59 g, 45.4 mmol) was added. The solution was stirred at room temperature overnight. 300 mL of EtOAc and 300 mL of water were added. The organic layers were washed with 200 mL 1N HCl solution, dried over Na2SO4 and concentrated. The residue was pure product (12.5 g, quant. yield). 1H NMR (CDCl3 400 MHz) δ 7.30 (d, J=8.8 Hz, 2H), 7.24 (d, J=8.8 Hz, 2H), 7.03 (m, 1H), 6.77 (m, 1H), 4.08 (s, 2H).

Workup

  1. washThe organic layers were washed with 200 mL 1N HCl solution
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4f3018bba963405d92f99816b5611df0
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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