2-Bromo-naphtho[2,3-b]furan-4,9-dione → 2-Methylthio-naphtho[2,3-b]furan-4,9-dione

HRID 540652Notes

Reaction equation

HRID 540652 reaction equation
Br[C:2]1[O:6][C:5]2[C:7](=[O:16])[C:8]3[C:13]([C:14](=[O:15])[C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C(S)[CH2:18][S:19]([O-])(=O)=O.[Na+]>O1CCCC1.O>[CH3:18][S:19][C:2]1[O:6][C:5]2[C:7](=[O:16])[C:8]3[C:13]([C:14](=[O:15])[C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

5

Reactant 2

HCID 3962872-Bromo-naphtho[2,3-b]furan-4,9-dioneHCID 23662354Mesna

Product 1

HCID 107766732-Methylthio-naphtho[2,3-b]furan-4,9-dioneYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 0.7 gram (2.5 mmoles) of 2-bromo-naphtho[2,3-b]furan-4,9-dione in 20 mL of tetrahydrofuran at room temperature, 0.4 grams (5.0 mmoles) of MeSNa in 5 mL of water was added dropwise over 1 minute. The mixture was further stirred for 2 hours at room temperature, and then evaporated to remove tetrahydrofuran. To the residue, 20 mL of 1N hydrochloric acid was added, and the resulting mixture was filtered. The solid was washed with water, and then crystallized in ethanol/water. Pure crystal product was filtered and dried under vacuum. 0.55 grams of product (yield 90%) was obtained and characterized by 1H NMR and mass spectrum. 1H NMR (in CDCl3) δ 2.66 (s, 3H), 6.79 (s, 1H), 7.75-7.79 (m, 2H), 8.18-8.25 (m, 2H). Mass (M+H) is 245.

Workup

  1. customevaporated
  2. customto remove tetrahydrofuran
  3. additionTo the residue, 20 mL of 1N hydrochloric acid was added
  4. filtrationthe resulting mixture was filtered
  5. washThe solid was washed with water
  6. customcrystallized in ethanol/water
  7. filtrationPure crystal product was filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-ced5cc5c55bd4c3b8a67026cd95b98e1
Source dataset
uspto-grants-2014_10
Patent number
US08871802B2

Reaction notes

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