Thiophenol → HCID 13600407, compound

HRID 1651141Notes

Reaction equation

HRID 1651141 reaction equation
Br[CH:2]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:9](=[O:17])[C:8]2[C:7]([OH:18])=[CH:6][CH:5]=[CH:4][C:3]1=2.[C:19]1([SH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[OH:18][C:7]1[C:8]2[C:9](=[O:17])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][C:11]=3[OH:16])[CH:2]([S:25][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 27650410-Bromo-1,8-dihydroxy-10H-anthracen-9-one

Product 1

HCID 13600407HCID 13600407, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10-Bromo-1,8-dihydroxy-9-anthrone (3.05 g) was dissolved in dichloromethane (100 ml) and thiophenol (1.1 ml) was added. The red-brown solution became yellow-green, and was then left, with stirring, at room temperature for 5 hours. Removal of the solvent gave a yellow solid which, after recrystallisation from a hexane/chloroform mixture (10:1), afforded 1,8-dihydroxy-10-phenylthio-9-anthrone (2.89 g, 87%) as pale yellow needles, melting point 156°-157° C. (Found: C 71.8, H 4.2, S 9.95; C20H14O3S requires C 71.85, H 4.2, S 9.6%.)

Workup

  1. waitwas then left
  2. customRemoval of the solvent
  3. customgave a yellow solid which
  4. customafter recrystallisation from a hexane/chloroform mixture (10:1)

Sources & evidence

ORD record
ord-bb896726db814644b070e51037764c70
Source dataset
uspto-grants-1990_05
Patent number
US04927845

Reaction notes

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