p-Chlorothiophenol → (4-Chlorophenyl)(2,5-difluorobenzyl)sulfane

HRID 2080353Notes

Reaction equation

HRID 2080353 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[F:42][C:43]1[CH:50]=[CH:49][C:48]([F:51])=[CH:47][C:44]=1[CH2:45]O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:45][C:44]2[CH:47]=[C:48]([F:51])[CH:49]=[CH:50][C:43]=2[F:42])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7815p-ChlorothiophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5225992,5-Difluorobenzyl alcohol

Product 1

HCID 16681304(4-Chlorophenyl)(2,5-difluorobenzyl)sulfaneYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., 4-chlorobenzenethiol (5.45 g, 38.2 mmol), triphenylphosphine (11.1 g, 41.6 mmol) and diisopropyl azodicarboxylate (8.16 ml, 41.6 mmol) were sequentially added to a tetrahydrofuran (150 ml) solution of 2,5-difluorobenzyl alcohol (5.00 g, 34.7 mmol). The reaction mixture was stirred at room temperature for 4 days, followed by concentration. The residue thus obtained was purified by silica gel column chromatography (1% ethyl acetate-hexane) to give 2-[(4-chlorophenyl)thiomethyl]-1,4-difluorobenzene (2.68 g, 29%) as a colorless oil.

Workup

  1. concentrationfollowed by concentration
  2. customThe residue thus obtained
  3. customwas purified by silica gel column chromatography (1% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-5634f7f74c8a4e2c853be4e8d1ff6274
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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