Iodine → 1,1'-disulfanediylbis(2-bromobenzene)

HRID 1977925Notes

Reaction equation

HRID 1977925 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[OH-].[Na+].II>C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 805982-Bromobenzenethiol

Product 1

HCID 2334811,1'-disulfanediylbis(2-bromobenzene)Yield 86.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 2-bromothiophenol (20.0 g, 106 mmol) and 2N sodium hydroxide solution (100 mL) in diethyl ether (400 mL) was added solid iodine (13.4 g, 53.0 mmol) in portions. The mixture was stirred at room temperature for 1 hour at which time the ether layer was separated. The aqueous layer was extracted with a fresh portion of ether and the combined ether layers were washed once with water, once with a saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 17.2 g (43%) of intermediate product as a white solid: mp 95-97° C.; NMR (CDCl3) 7.52 (m, 4H), 7.25 (t, J=9.7 Hz, 2H), 7.06 (t, J=9.7 Hz, 2H); MS-FD m/e 380 (p+4, 20), 379 (p+3, 30), 378 (p+2, 85), 376 (p, 100), 374 (p−2, 75); IR.

Workup

  1. customwas separated
  2. extractionThe aqueous layer was extracted with a fresh portion of ether
  3. washthe combined ether layers were washed once with water, once with a saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-159b530083514d1bb6b72cfc8c50d9ec
Source dataset
uspto-grants-2001_05
Patent number
US06235785B1

Reaction notes

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