Bromobenzene → Diphenyl sulfide

HRID 1884204Notes

Reaction equation

HRID 1884204 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1([SH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O(C(C)(C)C)[Na]>C1(C)C=CC=CC=1>[C:2]1([S:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 7969ThiophenolHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 8766Diphenyl sulfide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 50 mL of reactor equipped with magnetic stir bar was charged with 252 mg (0.27 mmol) of {[(t-Bu)2P(OH)]2PdCl}2, 2.90 g (18.47 mmol) of bromobenzene, 1.98 g (18.0 mmol) of PhSH and 3.46 g (36.0 mmol) of NaO—tBu in 20.0 mL of toluene. The resulting mixture was refluxed for 15 h before the mixture was cooled to room temperature and quenched with 100 mL of H2O. The mixture was transferred to a separatory funnel, and extracted with EtOAc (2×200 mL). The layers were separated, and organic layer was washed with H2O (100 mL), brine (150 mL), and dried over mgSO4, filtered, and the solvents removed from the filtrate by rotary evaporation. The product was isolated by distillation. The final product was obtained as a colorless oil (2.24 g, 66% yield).

Workup

  1. customA 50 mL of reactor equipped with magnetic stir bar
  2. temperatureThe resulting mixture was refluxed for 15 h before the mixture
  3. customquenched with 100 mL of H2O
  4. customThe mixture was transferred to a separatory funnel
  5. extractionextracted with EtOAc (2×200 mL)
  6. customThe layers were separated
  7. washorganic layer was washed with H2O (100 mL), brine (150 mL)
  8. customdried over mgSO4
  9. filtrationfiltered
  10. customthe solvents removed from the filtrate by rotary evaporation
  11. customThe product was isolated by distillation

Sources & evidence

ORD record
ord-e631242a7bb340fa9f26c4262d7576ec
Source dataset
uspto-grants-2004_07
Patent number
US06762330B2

Reaction notes

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