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

HRID 1047478Notes

Reaction equation

HRID 1047478 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-bac4f6d79f244821ab812c5f43b4bfa2
Source dataset
uspto-grants-2013_10
Patent number
US08569521B2

Reaction notes

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