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

HRID 2080354Notes

Reaction equation

HRID 2080354 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[F:16].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][CH:19]=1.[Cl-].[NH4+]>O.CN(C)C=O>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24][CH2:8][C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[F:16])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 5228302-(Bromomethyl)-1,4-difluorobenzene

Product 1

HCID 16681304(4-Chlorophenyl)(2,5-difluorobenzyl)sulfaneYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

After addition of potassium carbonate (4.00 g, 29.0 mmol) and 2-bromomethyl-1,4-difluorobenzene (5.00 g, 24.2 mmol) to an N,N-dimethylformamide (120 ml) solution of 4-chlorobenzenethiol (3.86 g, 26.6 mmol), the resulting mixture was stirred at room temperature for 3 hours. To the reaction mixture were added saturated ammonium chloride (50 ml) and water (20 ml), followed by extraction with diethyl ether. The extracts were combined, washed with water and brine, dried (over MgSO4), and concentrated. The residue thus obtained was purified by silica gel column chromatography (1% ethyl acetate-hexane) to give 2-[(4-chlorophenyl)thiomethyl]-1,4-difluorobenzene (6.41 g, 98%) as a colorless oil.

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. washwashed with water and brine
  3. dry with materialdried (over MgSO4)
  4. concentrationconcentrated
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography (1% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-d3034ff6a8a74a35be5913d0a8f3f41b
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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