2-Naphthalenethiol → HCID 19764842, compound

HRID 846681Notes

Reaction equation

HRID 846681 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[SH:11].I[C:13]1[CH:14]=[C:15]([Br:19])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1

Participants

5

Reactant 3

HCID 70582-NaphthalenethiolHCID 11430Potassium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-

Product 1

HCID 19764842HCID 19764842, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-naphthalenethiol (3.2 g), 3-iodobromobenzene (6.7 g), potassium carbonate (1.4 g), cuprous chloride (0.4 g) and DMF (4 ml) was heated to reflux for 1 hour. The mixture was allowed to cool to ambient temperature and was partitioned between diethyl ether and water. The mixture was filtered and the organic layer was separated, dried (MgSO4) and evaporated. The residue was taken up in ethyl acetate, decolourised by treatment with charcoal, reisolated and purified by recrystallisation from methanol to give 3-bromophenyl 2-naphthyl sulphide (3.9 g, 65%), m.p. 68°-70° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. customwas partitioned between diethyl ether and water
  4. filtrationThe mixture was filtered
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. custompurified by recrystallisation from methanol

Sources & evidence

ORD record
ord-9d02100d9eda433ab29f24da7586f414
Source dataset
uspto-grants-1992_08
Patent number
US05137913

Reaction notes

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