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

HRID 2212359Notes

Reaction equation

HRID 2212359 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=1[CH2:12]Br.C(N(CC)CC)C>ClCCl>[F:9][C:10]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=1[CH2:12][S:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 8471TriethylamineHCID 5228302-(Bromomethyl)-1,4-difluorobenzene

Product 1

HCID 16681304(4-Chlorophenyl)(2,5-difluorobenzyl)sulfaneYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Chlorothiophenol (3.6 g, 0.025 mol) in dichloromethane (100 mL) was treated with 2,5-difluorobenzyl bromide (5.17 g, 0.025 mol) and triethylamine (3.9 ml, 0.028 mol). The reaction was stirred for 2 hours then diluted with dichloromethane (250 mL) and washed with water (100 mL) and brine (100 mL). The separated organic layer was dried (MgSO4), evaporated to dryness, and the product purified by passing down a plug of silica eluting with hexane-ethyl acetate mixtures to give 4-chlorophenyl 2,5-difluorobenzyl sulfide (5.12 g). 1H NMR CDCl3 7.23 (4H, s), 6.69–6.86 (3H, m) and 4.04 (2H, s).

Workup

  1. washwashed with water (100 mL) and brine (100 mL)
  2. dry with materialThe separated organic layer was dried (MgSO4)
  3. customevaporated to dryness
  4. customthe product purified

Sources & evidence

ORD record
ord-a08731bc3156449faa00170ae1eed6ef
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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