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

HRID 1746926Notes

Reaction equation

HRID 1746926 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 1 N 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 1 N 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-750de272214d435c985ae4a6586fae66
Source dataset
uspto-grants-2015_10
Patent number
US09150530B2

Reaction notes

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