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

HRID 1746925Notes

Reaction equation

HRID 1746925 reaction equation
C[Si](C)(C)[C:3]1[O:7][C:6]2[C:8](=[O:17])[C:9]3[C:14]([C:15](=[O:16])[C:5]=2[CH:4]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[Br:20]Br>C(#N)C>[Br:20][C:3]1[O:7][C:6]2[C:8](=[O:17])[C:9]3[C:14]([C:15](=[O:16])[C:5]=2[CH:4]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

4

Reactant 2

HCID 24408BromineHCID 108496662-Trimethylsilyl-naphtho[2,3-b]furan-4,9-dione

Product 1

HCID 3962872-Bromo-naphtho[2,3-b]furan-4,9-dioneYield 90.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To the solution of 0.8 gram (3.0 mmoles) of 2-trimethylsilyl-naphtho[2,3-b]furan-4,9-dione in 20 mL of acetonitrile at room temperature, 0.53 grams (3.3 mmoles) of bromine in 20 mL of acetonitrile was added dropwise over 5 minutes. The mixture was further stirred for 30 minutes at room temperature, and then evaporated to dryness. The residue was crystallized in ethanol/water. Pure crystal product was filtered and dried under vacuum. 0.75 grams of product (yield 90%) was obtained and characterized by 1H NMR and mass spectrum. 1H NMR (in CDCl3) δ 6.96 (s, 1H), 7.76-7.82 (m, 2H), 8.18-8.25 (m, 2H). Mass (M+H) is 277 and 279.

Workup

  1. customevaporated to dryness
  2. customThe residue was crystallized in ethanol/water
  3. filtrationPure crystal product was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-52f28cb10b2042dc9c02479b5da646e6
Source dataset
uspto-grants-2015_10
Patent number
US09150530B2

Reaction notes

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