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

HRID 748665Notes

Reaction equation

HRID 748665 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+]>CN(C)C=O.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)sulfane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Process 2: After addition of potassium carbonate (4.00 g, 29.0 mmol) and 2-bromomethyl-1,4-difluorobenzene (5.00 g, 24.2 mmol) to a solution of 4-chlorobenzenethiol (3.86 g, 26.6 mmol) in N,N-dimethylformamide (120 ml), the mixture was stirred for 3 hours at room temperature. 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 chromatography on a silica gel column (1% ethyl acetate-hexane), whereby the title compound (6.41 g, 98%) was obtained 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 chromatography on a silica gel column (1% ethyl acetate-hexane), whereby the title compound (6.41 g, 98%)
  7. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-e849e1f639d04014a83c817be3fa06c3
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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